Dialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-diones, their preparation and their use

ABSTRACT

Dialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-diones of the formula (I) ##STR1## in which A represents alkyl which is optionally substituted by halogen and 
     B represents C 2  -C 10  -alkyl or 
     A and B together with the carbon atom to which they are bonded represent an unsubstituted cycle, 
     G represents hydrogen, 
     L and M represent oxygen and/or sulphur. These compounds possess herbicidal and pesticidal activity.

This application is a divisional, of application Ser. No. 08/200,138,filed Feb. 22, 1994 now U.S. Pat. No. 5,504,057.

The invention relates to noveldialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-diones, to processesfor their preparation and to their use as pesticides (in particular asinsecticides and acaricides) and as herbicides.

3-Acyl-pyrrolidine-2,4-diones have previously been described as havingpharmaceutical properties (S. Suzuki et al. Chem. Pharm. Bull. 15 1120(1967)). Furthermore, N-phenyl-pyrrolidine-2,4-diones were synthesizedby R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985 1095). Abiological activity of these compounds has not been described.

EP-A 0,262,399 discloses compounds of a similar structure(3-aryl-pyrrolidine-2,4-diones), from which, however, no herbicidal,insecticidal or acaricidal activity has been disclosed. Unsubstituted,bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 355,599 and EP415,211), substituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives(EP 501,129) and substituted mono-cyclic 3-aryl-pyrrolidine-2,4-dionederivatives (EP-A 377,893, EP 442,077 and EP 497,127) are known and havea herbicidal, insecticidal or acaricidal activity.

Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP442,073) and 1-H-3-arylpyrrolidine-dione derivatives (EP 456,063 and EP521,334).

Novel dialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-diones of theformula (I) ##STR2## have now been found, in which

A represents alkyl which is optionally substituted by halogen and

B represents C₂ -C₁₀ -alkyl or

A and B together with the carbon atom to which they are bonded representan unsubstituted cycle,

G represents hydrogen (a) or the groups ##STR3## E represents a metalion equivalent or an ammonium ion, L and M represents oxygen and/orsulphur,

R¹ represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, alkyl-thioalkyl, polyalkoxyalkyl or cycloalkyl, itbeing possible for the latter to be interrupted by hetero atoms, orrepresents optionally substituted phenyl, optionally substitutedphenylalkyl, substituted hetaryl, substituted phenoxyalkyl orsubstituted hetaryloxyalkyl,

R² represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionallysubstituted cycloalkyl, phenyl or benzyl,

R³, R⁴ and R⁵ independently of one another represent in each caseoptionally halogen-substituted alkyl, alkoxy, cycloalkyloxy, alkylamino,dialkylamino, alkylthio, alkenylthio or cycloalkylthio and in each caseoptionally substituted phenyl, phenoxy, benzyloxy or phenylthio,

R⁶ and R⁷ independently of one another represent hydrogen, in each caseoptionally halogen-substituted alkyl, alkenyl, alkoxy or alkoxy-alkyl,optionally substituted phenyl, optionally substituted benzyl, ortogether with the N-atom to which they are bound represent a cycle whichis optionally interrupted by oxygen or sulphur.

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G in the general formula (I), the following mainstructures (Ia) to (Ig) result: ##STR4## in which A, B, E, L, M, R¹, R²,R³, R⁴, R⁵, R⁶ and R⁷ have the abovementioned meanings.

Due to one or more centres of chirality, the compounds of the formula(Ia)-(Ig) are generally obtained as a mixture of stereoisomers which, ifappropriate, can be separated in the customary manner. They can be usedin the form of their diastereomer mixture and also as pure diastereomersor enantiomers. The following text will always mention compounds of theformula (Ia) to (Ig), for simplicity's sake, even though this is to beunderstood as meaning the pure compounds and also the mixturescontaining various proportions of isomeric, enantiomeric and stereomericcompounds.

Furthermore, it has been found that the noveldialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-diones of the formula(I) are obtained by one of the processes described below.

(A) Dialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-diones or theirenols of the formula (Ia) ##STR5## in which A and B have theabovementioned meaning, are obtained when N-acylamino acid esters of theformula (II) ##STR6## in which A and B have the abovementioned meaningand

R⁸ represents alkyl,

are subjected to an intramolecular condensation reaction in the presenceof a diluent and in the presence of a base; or

(B) compounds of the formula (Ib) ##STR7## in which A, B and R¹ have theabovementioned meaning, are obtained when compounds of the formula (Ia)##STR8## in which A and B have the abovementioned meaning,

are reacted

α) with acid halides of the general formula (III) ##STR9## in which R¹has the abovementioned meaning and

Hal represents halogen, in particular chlorine and bromine,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, or

β) with carboxylic anhydrides of the general formula (IV)

    R.sup.1 --CO--O--CO--R.sup.1                               (IV)

in which

R¹ has the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent; or

(C) compounds of the formula (Ic-1) ##STR10## in which A, B and R² havethe abovementioned meaning, and

M represents oxygen or sulphur, are obtained when compounds of theformula (Ia) ##STR11## in which A and B have the abovementioned meaning,

are reacted with chloroformic ester or chloroformic thioester of thegeneral formula (V)

    R.sup.2 --M--CO--Cl                                        (V)

in which

R² and M have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent; or

(D) compounds of the formula (Ic-2) ##STR12## in which A, B and R² havethe abovementioned meaning and

M represents oxygen or sulphur,

are obtained when compounds of the formula (Ia) ##STR13## in which A andB have the abovementioned meaning, are reacted

α) with chloromonothioformic esters or chlorodithioformic esters of thegeneral formula (VI) ##STR14## in which M and R² have the abovementionedmeaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, or

β) with carbon disulphide and subsequently with alkyl halides of thegeneral formula (VII)

    R.sup.2 --Hal                                              (VII)

in which

R² has the abovementioned meaning and

Hal represents chlorine, bromine or iodine,

if appropriate in the presence of a diluent; or

(E) compounds of the formula (Id) ##STR15## in which A, B and R³ havethe abovementioned meaning,

are obtained when compounds of the formula (Ia) ##STR16## in which A andB have the abovementioned meaning,

are reacted with sulphonyl chlorides of the general formula (VIII)

    R.sup.3 --SO.sub.2 --Cl                                    (VIII)

in which

R³ has the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent; or

(F) compounds of the formula (Ie) ##STR17## in which A, B, L, R⁴ and R⁵have the abovementioned meaning,

are obtained when 1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-diones ofthe formula (Ia) or their enols ##STR18## in which A and B have theabovementioned meaning,

are reacted with phosphorus compounds of the general formula (IX)##STR19## in which L, R⁴ and R⁵ have the abovementioned meaning and

Hal represents halogen, in particular chlorine and bromine,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent; or

(G) compounds of the formula (If) ##STR20## in which A and B have theabovementioned meaning and

E represents a metal ion equivalent or an ammonium ion,

are obtained when compounds of the formula (Ia) ##STR21## in which A andB have the abovementioned meaning,

are reacted with metal hydroxides or amines of the general formulae (X)and (XI) ##STR22## in which Me represents mono- or divalent metal ions,

t represent the number 1 or 2 and

R¹⁰, R¹¹ and R¹² independently of one another represent hydrogen oralkyl,

if appropriate in the presence of a diluent.

(H) Furthermore, it has been found that compounds of the formula (I)##STR23## in which A, B, L, R⁶ and R⁷ have the abovementioned meaning,are obtained when compounds of the formula (Ia) ##STR24## in which A andB have the abovementioned meaning,

are reacted

α) with compounds of the general formula (XII)

    R.sup.6 --N═C═L                                    (XII)

in which

L and R⁶ have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of a catalyst, or

β) with carbamoyl chlorides or thiocarbamoyl chlorides of the generalformula (XIII) ##STR25## in which L, R⁶ and R⁷ have the abovementionedmeaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent.

Furthermore, it has been found that the noveldialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-diones of the formula(I) are distinguished by outstanding insecticidal, acaricidal andherbicidal activities.

The following applies to the general formulae of the presentapplication:

A can preferably represent straight-chain or branched C₁ -C₁₀ -alkylwhich is optionally substituted by halogen,

B can preferably represent straight-chain or branched C₂ -C₁₀ -alkyl, or

A, B and the carbon atom to which they are bonded can preferablyrepresent an unsubstituted C₃ -C₁₂ -spiro cycle,

A particularly preferably represents straight-chain or branched C₁ -C₈-alkyl which is optionally substituted by fluorine and/or chlorine,

B particularly preferably represents straight-chain or branched C₂ -C₈-alkyl or

A, B and the carbon atom to which they are bonded particularlypreferably represent an unsubstituted C₃ -C₈ -spiro cycle,

A very particularly preferably represents straight-chain or branched C₁-C₆ -alkyl which is optionally substituted by fluorine,

B very particularly preferably represents straight-chain or branched C₂-C₄ -alkyl or

A, B and the carbon atom to which they are bonded very particularlypreferably represent an unsubstituted C₃ -C₇ -spiro cycle,

G preferably represents hydrogen (a) or the groups ##STR26## in which Erepresents a metal ion equivalent or an ammonium ion and

L and M in each case represent oxygen and/or sulphur,

R¹ represents in each case optionally halogen-substituted C₁ -C₂₀-alkyl, C₂ -C₂₀ -alkenyl, C₁ -C₈ -alkoxy-C₁ -C₈ -alkyl, C₁ -C₈-alkylthio-C₁ -C₈ -alkyl, C₁ -C₈ -polyalkoxy-C₁ -C₈ -alkyl or cycloalkylhaving 3 to 8 ring atoms, it being possible for the latter to beinterrupted by oxygen and/or sulphur atoms,

or represents phenyl which is optionally substituted by halogen, nitro,C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkyl, C₁ -C₆-halogenoalkoxy, C₁ -C₆ -alkylthio or C₁ -C₆ -alkylsulphonyl,

or represents phenyl-C₁ -C₆ -alkyl which is optionally substituted byhalogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkyl or C₁ -C₆-halogenoalkoxy,

or represents hetaryl which is optionally substituted by halogen and/orC₁ -C₆ -alkyl,

or represents phenoxy-C₁ -C₆ -alkyl which is optionally substituted byhalogen and/or C₁ -C₆ -alkyl,

or represents hetaryloxy-C₁ -C₆ -alkyl which is optionally substitutedby halogen, amino and/or C₁ -C₆ -alkyl,

R² represents C₁ -C₂₀ -alkyl, C₃ -C₂₀ -alkenyl, C₁ -C₈ -alkoxy-C₂ -C₈-alkyl or C₁ -C₈ -polyalkoxy-C₂ -C₈ -alkyl, each of which is optionallysubstituted by halogen,

or represents cycloalkyl, phenyl or benzyl, each of which is optionallysubstituted by halogen, nitro, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy or C₁ -C₆-halogenoalkyl,

R³, R⁴ and R⁵ independently of one another represent C₁ -C₈ -alkyl, C₁-C₈ -alkoxy, C₃ -C₇ -cycloalkyloxy, C₁ -C₈ -alkylamino, di-(C₁-C₈)-alkylamino, C₁ -C₈ -alkylthio, C₃ -C₈ -alkenylthio or C₃ -C₇-cycloalkylthio, each of which is optionally substituted by halogen, orrepresent phenyl, phenoxy, benzyloxy or phenylthio, each of which isoptionally substituted by halogen, nitro, cyano, C₁ -C₄ -alkoxy, C₁ -C₄-halogenoalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -halogenoalkylthio, C₁ -C₄-alkyl or C₁ -C₄ -halogenoalkyl,

R⁶ and R⁷ independently of one another represent hydrogen or representC₁ -C₈ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₈ -alkoxy, C₃ -C₈ -alkenyl or C₁-C₈ -alkoxy-C₂ -C₈ -alkyl, each of which is optionally substituted byhalogen, or represent phenyl which is optionally substituted by halogen,C₁ -C₈ -halogenoalkyl, C₁ -C₈ -alkyl or C₁ -C₈ -alkoxy, or representbenzyl which is optionally substituted by halogen, C₁ -C₈ -alkyl, C₁ -C₈-halogenoalkyl or C₁ -C₈ -alkoxy, or together with the N-atom to whichthey are bound represent a ring having 3-6 C-atoms which is optionallyinterrupted by oxygen or sulphur,

G particularly preferably represents hydrogen (a) or the groups##STR27## in which E represents a metal ion equivalent or an ammoniumion,

L and M in each case represent oxygen and/or sulphur,

R¹ represents in each case optionally halogen-substituted C₁ -C₁₆-alkyl, C₂ -C₁₆ -alkenyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₁₆-alkylthio-C₁ -C₆ -alkyl, C₁ -C₆ -polyalkoxy-C₁ -C₆ -alkyl or cycloalkylhaving 3 to 7 ring atoms which can be interrupted by 1-2 oxygen and/orsulphur atoms,

or represents phenyl which is optionally substituted by halogen, nitro,C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃ -halogenoalkyl, C₁ -C₃-halogenoalkoxy, C₁ -C₆ -alkylthio or C₁ -C₆ -alkylsulphonyl,

or represents phenyl-C₁ -C₄ -alkyl which is optionally substituted byhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃ -halogenoalkyl or C₁ -C₃-halogenoalkoxy,

or represents hetaryl which is optionally substituted by fluorine,chlorine, bromine- and/or C₁ -C₄ -alkyl,

or represents phenoxy-C₁ -C₅ -alkyl which is optionally substituted byfluorine, chlorine, bromine and/or C₁ -C₄ -alkyl,

or represents hetaryloxy-C₁ -C₅ -alkyl which is optionally substitutedby fluorine, chlorine, bromine, amino and/or C₁ -C₄ -alkyl,

R² represents C₁ -C₁₆ -alkyl, C₃ -C₁₆ -alkenyl, C₁ -C₆ -alkoxy-C₂ -C₆-alkyl or C₁ -C₆ -polyalkoxy-C₂ -C₆ -alkyl, each of which is optionallysubstituted by halogen,

or represents cycloalkyl, phenyl or benzyl, each of which is optionallysubstituted by halogen, nitro, C₁ -C₄ -alkyl, C₁ -C₃ -alkoxy or C₁ -C₃-halogenoalkyl,

R³, R⁴ and R⁵ independently of one another represent C₁ -C₆ -alkyl, C₁-C₆ -alkoxy, C₃ -C₆ -cycloalkyloxy, C₁ -C₆ -alkylamino, di-(C₁-C₆)-alkylamino, C₁ -C₆ -alkylthio, C₃ -C₆ -alkenylthio or C₃ -C₆-cycloalkylthio, each of which is optionally substituted by halogen, orrepresent phenyl, phenoxy, benzyloxy or phenylthio, each of which isoptionally substituted by fluorine, chlorine, bromine, nitro, cyano, C₁-C₃ -alkoxy, C₁ -C₃ -halogenoalkoxy, C₁ -C₃ -alkylthio, C₁ -C₃-halogenoalkylthio, C₁ -C₃ -alkyl or C₁ -C₃ -halogenoalkyl,

R⁶ and R⁷ independently of one another represent hydrogen, C₁ -C₆-alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyl or C₁ -C₆-alkoxy-C₂ -C₆ -alkyl, each of which is optionally substituted byhalogen, or represent phenyl which is optionally substituted by halogen,C₁ -C₅ -halogenoalkyl, C₁ -C₅ -alkyl or C₁ -C₅ -alkoxy, or representbenzyl which is optionally substituted by halogen, C₁ -C₅ -alkyl, C₁ -C₅-halogenoalkyl or C₁ -C₅ -alkoxy, or together with the N-atom to whichthey are bound, represent a ring having 3-6 C-atoms which is optionallyinterrupted by oxygen or sulphur.

G very particularly preferably represents hydrogen (a) or the groups##STR28## in which E represents a metal ion equivalent or an ammoniumion and

L and M represent oxygen and/or sulphur,

R¹ represents in each case optionally fluorine- or chlorine-substitutedC₁ -C₁₄ -alkyl, C₂ -C₁₄ -alkenyl, C₁ -C₄ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₄-alkylthio-C₁ -C₆ -alkyl, C₁ -C₄ -polyalkoxy-C₁ -C₄ -alkyl or cycloalkylhaving 3 to 6 ring atoms which can be interrupted by 1 to 2 oxygenand/or sulphur atoms,

or represents phenyl which is optionally substituted by fluorine,chlorine, bromine, methyl, ethyl,

propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy,nitro, methylthio, ethylthio., methylsulphonyl or ethylsulphonyl,

or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted byfluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy,ethoxy, trifluoromethyl or trifluoromethoxy,

or represents furanoyl, thienyl, pyridyl, pyrimidyl, thiazolyl andpyrazolyl, each of which is optionally substituted by fluorine,chlorine, bromine, methyl or ethyl,

or represents phenoxy-C₁ -C₄ -alkyl which is optionally substituted byfluorine, chlorine, methyl or ethyl,

or represents pyridyloxy-C₁ -C₄ -alkyl, pyrimidyloxy-C₁ -C₄ -alkyl andthiazolyloxy-C₁ -C₄ -alkyl, each of which is optionally substituted byfluorine, chlorine, amino, methyl or ethyl,

R² represents C₁ -C₁₄ -alkyl, C₃ -C₁₄ -alkenyl, C₁ -C₄ -alkoxy-C₂ -C₆-alkyl or C₁ -C₄ -polyalkoxy-C₂ -C₆ -alkyl, each of which is optionallysubstituted by fluorine or chlorine,

or represent cycloalkyl, phenyl or benzyl, each of which is optionallysubstituted by fluorine, chlorine, nitro, methyl, ethyl, propyl,i-propyl, methoxy, ethoxy or trifluoromethyl,

R³, R⁴ and R⁵ independently of one another represent C₁ -C₄ -alkyl, C₁-C₄ -alkoxy, C₁ -C₄ -alkylamino, di-(C₁ -C₄)-alkylamino or C₁ -C₄-alkylthio, each of which is optionally substituted by fluorine orchlorine, or represent phenyl, phenoxy, benzyloxy or phenylthio, each ofwhich is optionally substituted by fluorine, chlorine, bromine, nitro,cyano, C₁ -C₂ -alkoxy, C₁ -C₄ -fluoroalkoxy, C₁ -C₂ -alkylthio, C₁ -C₂-fluoroalkylthio or C₁ -C₃ -alkyl.

R⁶ and R⁷ independently of one another represent hydrogen, or representC₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxy, C₃ -C₄ -alkenyl or C₁-C₄ -alkoxy-C₂ -C₄ -alkyl, each of which is optionally substituted byfluorine, chlorine or bromine, or represent phenyl which is optionallysubstituted by fluorine, chlorine, bromine, C₁ -C₄ - halogenoalkyl, C₁-C₄ -alkyl or C₁ -C₄ -alkoxy, or represent benzyl which is optionallysubstituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄-halogenoalkyl or C₁ -C₄ -alkoxy, or together with the N-atom to whichthey are bound represent a ring having 4-6 C-atoms which is optionallyinterrupted by oxygen or sulphur.

If, according to process (A), ethylN-2,4-dimethylphenyl-acetyl-2-amino-2-methyl-butyrate is used, thecourse of the process according to the invention can be represented bythe following equation: ##STR29##

If, according to process (B) (variant α)3-(2,4-dimethylphenyl)-5-methyl-5-propyl-pyrrolidine-2,4-dione andpivaloyl chloride are used as starting substances, the course of theprocess according to the invention can be represented by the followingequation: ##STR30##

If, according to process B (variant β),3-(2,4-dimethylphenyl)-5,5-diethyl-pyrrolidine-2,4-dione and aceticanhydride are used as starting compounds, the course of the processaccording to the invention can be represented by the following equation:##STR31##

If, according to process (C),3-(2,4-dimethylphenyl)-5-sec.-butyl-5-methyl-pyrrolidine-2,4-dione andethoxy-ethyl chloroformate are used as starting compounds, the course ofthe process according to the invention can be represented by thefollowing equation: ##STR32##

If, according to process (D.sub.α),3-(2,4-dimethylphenyl)-5-isopropyl-5-methyl-pyrrolidine-2,4-dione andmethyl chloromonothioformate are used as starting materials, the courseof the reaction can be represented as follows: ##STR33##

If, according to process (D.sub.β), 3-(2,4-dimethylphenyl)-5,5-pentamethylenepyrrolidine-2,4-dione, carbondisulphide and methyl iodide are used as starting components, the courseof the reaction can be represented as follows: ##STR34##

If, according to process (E) 3-(2,4-dimethylphenyl)-5-isobutyl-5-methyl-pyrrolidine-2,4-dione andmethane-sulphonyl chloride are used as the starting material, the courseof the reaction can be represented by the following equation: ##STR35##

If, according to process (F),3-(2,4-dimethylphenyl)-5.5-dipropyl-pyrrolidine-2,4-dione and2,2,2-trifluoroethyl methanethio-chlorophosphonate are used as startingmaterials, the course of the reaction can be represented by thefollowing equation: ##STR36##

If, according to process (G),3-(2,4-dimethylphenyl)-5,5-diethyl-pyrrolidine-2,4-dione and NaOH areused as the components, the course of the process according to theinvention can be represented by the following equation: ##STR37##

If, according to process (H.sub.α),3-(2,4-dimethylphenyl)-5,5-hexamethylene-pyrrolidine-2,4-dione and ethylisocyanate are used as starting materials, the course of the reactioncan be represented by the following equation: ##STR38##

If, according to process (H.sub.β),3-(2,4-dimethylphenyl)-5-butyl-5-methyl-pyrrolidine-2,4-dione anddimethylcarbamoyl chloride are used as starting materials, the course ofthe reaction can be represented by the following equation: ##STR39##

Some of the compounds of the formula (II) ##STR40## in which A, B and R⁸have the abovementioned meaning, which are required as startingsubstances in processes (A) according to the invention, are known andthe subject-matter of a German Patent Application by the applicantcompany which has hitherto not been disclosed (P 42 36 400).

Acylamino acid esters of the formula (II) are obtained, for example,when amino acid derivatives of the formula (XIV) ##STR41## in which R9'represents hydrogen (XIVa) and alkyl (XIVb) and

A and B have the abovementioned meaning, are acylated with2,4-dimethylphenylacetyl chloride, of the formula (XV) ##STR42## (Chem.Reviews 52, 237-416 (1953); Bhattacharya, Indien J. Chem. 6, 341-5,1968) or when acylamino acids of the formula (IIa) ##STR43## in which Aand B have the abovementioned meaning and

R⁹ represents hydrogen are esterified (Chem. Ind. (London) 1568 (1968)).

Compounds of the formula (IIa) can be obtained, for example, from2,4-dimethylacetyl chloride, of the formula (XV), and amino acids of theformula (XIVa) by the method of Schotten-Baumann (Organikum [LaboratoryPractical in Organic Chemistry], 9th edition, 446 (1970) VEB DeutscherVerlag der Wissenschaften, Berlin).

Furthermore, the starting substances of the formula (II) ##STR44## inwhich A, B and R⁸ have the abovementioned meaning

which are used in the above process (A) can be prepared whenaminonitriles of the formula (XVI) ##STR45## in which A and B have theabovementioned meaning,

are reacted with 2,4-dimethylphenylacetyl chloride, of the formula (XV),##STR46## to give compounds of the formula (XVII) ##STR47## in which Aand B have the abovementioned meaning,

and these compounds are subsequently subjected to alcoholysis insulphuric acid.

Some of the compounds of the formula (XVII) are also known and thesubject-matter of a German Patent Application by the applicant companywhich has hitherto not been disclosed (P 42 36 400).

The following compounds of the formula (Ia) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples:

                  TABLE 1                                                         ______________________________________                                         ##STR48##                     I-a                                                    A     B                                                               ______________________________________                                                CH.sub.3                                                                            C.sub.2 H.sub.5                                                         CH.sub.3                                                                            C.sub.3 H.sub.7 -n                                                      CH.sub.3                                                                            C.sub.3 H.sub.7 -i                                                      CH.sub.3                                                                            C.sub.4 H.sub.9-n                                                       CH.sub.3                                                                            C.sub.4 H.sub.9 -i                                                      CH.sub.3                                                                            C.sub.4 H.sub.9 -s                                                      CH.sub.3                                                                            C.sub.4 H.sub.9 -t                                                      CH.sub.3                                                                            C.sub.5 H.sub.11                                                        CH.sub.3                                                                            C.sub.5 H.sub.11 -i                                                     C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                         C.sub.3 H.sub.7                                                                     C.sub.3 H.sub.7                                                         C.sub.3 H.sub.7 -i                                                                  C.sub.3 H.sub.7 -i                                                      (CH.sub.2).sub.2                                                              (CH.sub.2).sub.4                                                              (CH.sub.2).sub.5                                                              (CH.sub.2).sub.6                                                              (CH.sub.2).sub.7                                                      ______________________________________                                    

The following compounds of the formula (Ib) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples:

                  TABLE 2                                                         ______________________________________                                         ##STR49##                     I-b                                            A        B          R.sup.1                                                   ______________________________________                                        CH.sub.3 C.sub.2 H.sub.5                                                                          CH.sub.3                                                  CH.sub.3 C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                           CH.sub.3 C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -n                                        CH.sub.3 C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -i                                        CH.sub.3 C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9 -n                                        CH.sub.3 C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9 -i                                        CH.sub.3 C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9 -t                                        CH.sub.3 C.sub.2 H.sub.5                                                                          C(CH.sub.3).sub.2C.sub.2 H.sub.5                          CH.sub.3 C.sub.2 H.sub.5                                                                          C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       CH.sub.3 C.sub.2 H.sub.5                                                                          C(CH.sub.3).sub.2CH.sub.2Cl                               CH.sub.3 C.sub.2 H.sub.5                                                                          C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        CH.sub.3 C.sub.2 H.sub.5                                                                          CH.sub.2C.sub.4 H.sub.9 -t                                CH.sub.3 C.sub.2 H.sub.5                                                                           ##STR50##                                                CH.sub.3 C.sub.2 H.sub.5                                                                          CH.sub.2SCH.sub.3                                         CH.sub.3 C.sub.2 H.sub.5                                                                          CHC(CH.sub.3).sub.2                                       CH.sub.3 C.sub.2 H.sub.5                                                                           ##STR51##                                                CH.sub.3 C.sub.2 H.sub.5                                                                           ##STR52##                                                CH.sub.3 C.sub.2 H.sub.5                                                                           ##STR53##                                                CH.sub.3 C.sub.2 H.sub.5                                                                           ##STR54##                                                CH.sub.3 C.sub.2 H.sub.5                                                                           ##STR55##                                                CH.sub.3 C.sub.2 H.sub.5                                                                           ##STR56##                                                CH.sub.3 C.sub.3 H.sub.7                                                                          CH.sub.3                                                  CH.sub.3 C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                           CH.sub.3 C.sub.3 H.sub.7                                                                          C.sub.3 H.sub.7 -n                                        CH.sub.3 C.sub.3 H.sub.7                                                                          C.sub.3 H.sub.7 -i                                        CH.sub.3 C.sub.3 H.sub.7                                                                          C.sub.4 H.sub.9 -n                                        CH.sub.3 C.sub.3 H.sub.7                                                                          C.sub.4 H.sub.9 -i                                        CH.sub.3 C.sub.3 H.sub.7                                                                          C.sub.4 H.sub.9 -t                                        CH.sub.3 C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2C.sub.2 H.sub.5                          CH.sub.3 C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       CH.sub.3 C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2CH.sub.2Cl                               CH.sub.3 C.sub.3 H.sub.7                                                                          C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        CH.sub.3 C.sub.3 H.sub.7                                                                          CH.sub.2C.sub.4 H.sub.9 -t                                CH.sub.3 C.sub.3 H.sub.7                                                                           ##STR57##                                                CH.sub.3 C.sub.3 H.sub.7                                                                          CH.sub.2SCH.sub.3                                         CH.sub.3 C.sub.3 H.sub.7                                                                          CHC(CH.sub.3).sub.2                                       CH.sub.3 C.sub.3 H.sub.7                                                                           ##STR58##                                                CH.sub.3 C.sub.3 H.sub.7                                                                           ##STR59##                                                CH.sub.3 C.sub.3 H.sub.7                                                                           ##STR60##                                                CH.sub.3 C.sub.3 H.sub.7                                                                           ##STR61##                                                CH.sub.3 C.sub.3 H.sub.7                                                                           ##STR62##                                                CH.sub.3 C.sub.3 H.sub.7                                                                           ##STR63##                                                CH.sub.3 C.sub.3 H.sub.7 -i                                                                       CH.sub.3                                                  CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C.sub.2 H.sub.5                                           CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C.sub.3 H.sub.7 -n                                        CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C.sub.3 H.sub.7 -i                                        CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C.sub.4 H.sub.9 -n                                        CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C.sub.4 H.sub.9 -i                                        CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C.sub.4 H.sub.9 -t                                        CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C(CH.sub.3).sub.2C.sub.2 H.sub.5                          CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C(CH.sub.3).sub.2CH.sub.2Cl                               CH.sub.3 C.sub.3 H.sub.7 -i                                                                       C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        CH.sub.3 C.sub.3 H.sub.7 -i                                                                       CH.sub.2C.sub.4 H.sub.9 -t                                CH.sub.3 C.sub.3 H.sub.7 -i                                                                        ##STR64##                                                CH.sub.3 C.sub.3 H.sub.7 -i                                                                       CH.sub.2SCH.sub.3                                         CH.sub.3 C.sub.3 H.sub.7 -i                                                                       CHC(CH.sub.3).sub.2                                       CH.sub.3 C.sub.3 H.sub.7 -i                                                                        ##STR65##                                                CH.sub.3 C.sub.3 H.sub.7 -i                                                                        ##STR66##                                                CH.sub.3 C.sub.3 H.sub.7 -i                                                                        ##STR67##                                                CH.sub.3 C.sub.3 H.sub.7 -i                                                                        ##STR68##                                                CH.sub.3 C.sub.3 H.sub.7 -i                                                                        ##STR69##                                                CH.sub.3 C.sub.3 H.sub.7 -i                                                                        ##STR70##                                                CH.sub.3 C.sub.4 H.sub.9                                                                          CH.sub.3                                                  CH.sub.3 C.sub.4 H.sub.9                                                                          C.sub.2 H.sub.5                                           CH.sub.3 C.sub.4 H.sub.9                                                                          C.sub.3 H.sub.7 -n                                        CH.sub.3 C.sub.4 H.sub.9                                                                          C.sub.3 H.sub.7 -i                                        CH.sub.3 C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9 -n                                        CH.sub.3 C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9 -i                                        CH.sub.3 C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9 -t                                        CH.sub.3 C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.2C.sub.2 H.sub.5                          CH.sub.3 C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       CH.sub.3 C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.2CH.sub.2Cl                               CH.sub.3 C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        CH.sub.3 C.sub.4 H.sub.9                                                                          CH.sub.2C.sub.4 H.sub.9 -t                                CH.sub.3 C.sub.4 H.sub.9                                                                           ##STR71##                                                CH.sub.3 C.sub.4 H.sub.9                                                                          CH.sub.2SCH.sub.3                                         CH.sub.3 C.sub.4 H.sub.9                                                                          CHC(CH.sub.3).sub.2                                       CH.sub.3 C.sub.4 H.sub.9                                                                           ##STR72##                                                CH.sub.3 C.sub.4 H.sub.9                                                                           ##STR73##                                                CH.sub.3 C.sub.4 H.sub.9                                                                           ##STR74##                                                CH.sub.3 C.sub.4 H.sub.9                                                                           ##STR75##                                                CH.sub.3 C.sub.4 H.sub.9                                                                           ##STR76##                                                CH.sub.3 C.sub.4 H.sub.9                                                                           ##STR77##                                                CH.sub.3 C.sub.4 H.sub.9 -i                                                                       CH.sub.3                                                  CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C.sub.2 H.sub.5                                           CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C.sub.3 H.sub.7 -n                                        CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C.sub.3 H.sub.7 -i                                        CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C.sub.4 H.sub.9 -n                                        CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C.sub.4 H.sub.9 -i                                        CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C.sub.4 H.sub.9 -t                                        CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C(CH.sub.3).sub.2C.sub.2 H.sub.5                          CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C(CH.sub.3).sub.2CH.sub.2Cl                               CH.sub.3 C.sub.4 H.sub.9 -i                                                                       C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        CH.sub.3 C.sub.4 H.sub.9 -i                                                                       CH.sub.2C.sub.4 H.sub.9 -t                                CH.sub.3 C.sub.4 H.sub.9 -i                                                                        ##STR78##                                                CH.sub.3 C.sub.4 H.sub.9 -i                                                                       CH.sub.2SCH.sub.3                                         CH.sub.3 C.sub.4 H.sub.9 -i                                                                       CHC(CH.sub.3).sub.2                                       CH.sub.3 C.sub.4 H.sub.9 -i                                                                        ##STR79##                                                CH.sub.3 C.sub.4 H.sub.9 -i                                                                        ##STR80##                                                CH.sub.3 C.sub.4 H.sub.9 -i                                                                        ##STR81##                                                CH.sub.3 C.sub.4 H.sub.9 -i                                                                        ##STR82##                                                CH.sub.3 C.sub.4 H.sub.9 -i                                                                        ##STR83##                                                CH.sub.3 C.sub.4 H.sub.9 -i                                                                        ##STR84##                                                CH.sub.3 C.sub.4 H.sub.9 -s                                                                       CH.sub.3                                                  CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C.sub.2 H.sub.5                                           CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C.sub.3 H.sub.7 -n                                        CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C.sub.3 H.sub.7 -i                                        CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C.sub.4 H.sub.9 -n                                        CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C.sub.4 H.sub.9 -i                                        CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C.sub.4 H.sub.9 -t                                        CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C(CH.sub.3).sub.2C.sub.2 H.sub.5                          CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C(CH.sub.3).sub.2CH.sub.2Cl                               CH.sub.3 C.sub.4 H.sub.9 -s                                                                       C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        CH.sub.3 C.sub.4 H.sub.9 -s                                                                       CH.sub.2C.sub.4 H.sub.9 -t                                CH.sub.3 C.sub.4 H.sub.9 -s                                                                        ##STR85##                                                CH.sub.3 C.sub.4 H.sub.9 -s                                                                       CH.sub.2SCH.sub.3                                         CH.sub.3 C.sub.4 H.sub.9 -s                                                                       CHC(CH.sub.3).sub.2                                       CH.sub.3 C.sub.4 H.sub.9 -s                                                                        ##STR86##                                                CH.sub.3 C.sub.4 H.sub.9 -s                                                                        ##STR87##                                                CH.sub.3 C.sub.4 H.sub.9 -s                                                                        ##STR88##                                                CH.sub.3 C.sub.4 H.sub.9 -s                                                                        ##STR89##                                                CH.sub.3 C.sub.4 H.sub.9 -s                                                                        ##STR90##                                                CH.sub.3 C.sub.4 H.sub.9 -s                                                                        ##STR91##                                                CH.sub.3 C.sub.4 H.sub.9 -t                                                                       CH.sub.3                                                  CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C.sub.2 H.sub.5                                           CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C.sub.3 H.sub.7 -n                                        CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C.sub.3 H.sub.7 -i                                        CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C.sub.4 H.sub.9 -n                                        CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C.sub.4 H.sub.9 -i                                        CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C.sub.4 H.sub.9 -t                                        CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C(CH.sub.3).sub.2C.sub.2 H.sub.5                          CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C(CH.sub.3).sub.2CH.sub.2Cl                               CH.sub.3 C.sub.4 H.sub.9 -t                                                                       C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        CH.sub.3 C.sub.4 H.sub.9 -t                                                                       CH.sub.2C.sub.4 H.sub.9 -t                                CH.sub.3 C.sub.4 H.sub.9 -t                                                                        ##STR92##                                                CH.sub.3 C.sub.4 H.sub.9 -t                                                                       CH.sub.2SCH.sub.3                                         CH.sub.3 C.sub.4 H.sub.9 -t                                                                       CHC(CH.sub.3).sub.2                                       CH.sub.3 C.sub.4 H.sub.9 -t                                                                        ##STR93##                                                CH.sub.3 C.sub.4 H.sub.9 -t                                                                        ##STR94##                                                CH.sub.3 C.sub.4 H.sub.9 -t                                                                        ##STR95##                                                CH.sub.3 C.sub.4 H.sub.9 -t                                                                        ##STR96##                                                CH.sub.3 C.sub.4 H.sub.9 -t                                                                        ##STR97##                                                CH.sub.3 C.sub.4 H.sub.9 -t                                                                        ##STR98##                                                C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          CH.sub.3                                                  C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                           C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -n                                        C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -i                                        C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9 -n                                        C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9 -i                                        C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9 -t                                        C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C(CH.sub.3).sub.2C.sub.2 H.sub.5                          C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C(CH.sub.3).sub.2CH.sub.2Cl                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          CH.sub.2C.sub.4 H.sub.9 -t                                C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                           ##STR99##                                                C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          CH.sub.2SCH.sub.3                                         C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          CHC(CH.sub.3).sub.2                                       C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                           ##STR100##                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                           ##STR101##                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                           ##STR102##                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                           ##STR103##                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                           ##STR104##                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                           ##STR105##                                               (CH.sub.2).sub.2    CH.sub.3                                                  (CH.sub.2).sub.2    C.sub.2 H.sub.5                                           (CH.sub.2).sub.2    C.sub.3 H.sub.7 -n                                        (CH.sub.2).sub.2    C.sub.3 H.sub.7 -i                                        (CH.sub.2).sub.2    C.sub.4 H.sub.9 -n                                        (CH.sub.2).sub.2    C.sub.4 H.sub.9 -i                                        (CH.sub.2).sub.2    C.sub.4 H.sub.9 -t                                        (CH.sub.2).sub.2    C(CH.sub.3).sub.2C.sub.2 H.sub.5                          (CH.sub.2).sub.2    C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       (CH.sub.2).sub.2    C(CH.sub.3).sub.2CH.sub.2Cl                               (CH.sub.2).sub.2    (CH.sub.3).sub.2CH.sub.2OCH.sub.3                         (CH.sub.2).sub.2    CH.sub.2C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.2                                                                                   ##STR106##                                               (CH.sub.2).sub.2    CH.sub.2SCH.sub.3                                         (CH.sub.2).sub.2    CHC(CH.sub.3).sub.2                                       (CH.sub.2).sub.2                                                                                   ##STR107##                                               (CH.sub.2).sub.2                                                                                   ##STR108##                                               (CH.sub.2).sub.2                                                                                   ##STR109##                                               (CH.sub.2).sub.2                                                                                   ##STR110##                                               (CH.sub.2).sub.2                                                                                   ##STR111##                                               (CH.sub.2).sub.2                                                                                   ##STR112##                                               (CH.sub.2).sub.4    CH.sub.3                                                  (CH.sub.2).sub.4    C.sub.2 H.sub.5                                           (CH.sub.2).sub.4    C.sub.3 H.sub.7 -n                                        (CH.sub.2).sub.4    C.sub.3 H.sub.7 -i                                        (CH.sub.2).sub.4    C.sub.4 H.sub.9 -n                                        (CH.sub.2).sub.4    C.sub.4 H.sub.9 -i                                        (CH.sub.2).sub.4    C.sub.4 H.sub.9 -t                                        (CH.sub.2).sub.4    C(CH.sub.3).sub.2C.sub.2 H.sub.5                          (CH.sub.2).sub.4    C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       (CH.sub.2).sub.4    C(CH.sub.3).sub.2CH.sub.2Cl                               (CH.sub.2).sub.4    C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        (CH.sub.2).sub.4    CH.sub.2C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.4                                                                                   ##STR113##                                               (CH.sub.2).sub.4    CH.sub.2SCH.sub.3                                         (CH.sub.2).sub.4    CHC(CH.sub.3).sub.2                                       (CH.sub.2).sub.4                                                                                   ##STR114##                                               (CH.sub.2).sub.4                                                                                   ##STR115##                                               (CH.sub.2).sub.4                                                                                   ##STR116##                                               (CH.sub.2).sub.4                                                                                   ##STR117##                                               (CH.sub.2).sub.4                                                                                   ##STR118##                                               (CH.sub.2).sub.4                                                                                   ##STR119##                                               (CH.sub.2).sub.5    CH.sub.3                                                  (CH.sub.2).sub.5    C.sub.2 H.sub.5                                           (CH.sub.2).sub.5    C.sub.3 H.sub.7 -n                                        (CH.sub.2).sub.5    C.sub.3 H.sub.7 -i                                        (CH.sub.2).sub.5    C.sub.4 H.sub.9 -n                                        (CH.sub.2).sub.5    C.sub.4 H.sub.9 -i                                        (CH.sub.2).sub.5    C.sub.4 H.sub.9 -t                                        (CH.sub.2).sub.5    C(CH.sub.3).sub.2C.sub.2 H.sub.5                          (CH.sub.2).sub.5    C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       (CH.sub.2).sub.5    C(CH.sub.3).sub.2CH.sub.2Cl                               (CH.sub.2).sub.5    C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        (CH.sub.2).sub.5    CH.sub.2C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.5                                                                                   ##STR120##                                               (CH.sub.2).sub.5    CH.sub.2SCH.sub.3                                         (CH.sub.2).sub.5    CHC(CH.sub.3).sub.2                                       (CH.sub.2).sub.5                                                                                   ##STR121##                                               (CH.sub.2).sub.5                                                                                   ##STR122##                                               (CH.sub.2).sub.5                                                                                   ##STR123##                                               (CH.sub.2).sub.5                                                                                   ##STR124##                                               (CH.sub.2).sub.5                                                                                   ##STR125##                                               (CH.sub.2).sub.5                                                                                   ##STR126##                                               (CH.sub.2).sub.6    CH.sub.3                                                  (CH.sub.2).sub.6    C.sub.2 H.sub.5                                           (CH.sub.2).sub.6    C.sub.3 H.sub.7 -n                                        (CH.sub.2).sub.6    C.sub.3 H.sub.7 -i                                        (CH.sub.2).sub.6    C.sub.4 H.sub.9 -n                                        (CH.sub.2).sub.6    C.sub.4 H.sub.9 -i                                        (CH.sub.2).sub.6    C.sub.4 H.sub.9 -t                                        (CH.sub.2).sub.6    C(CH.sub.3).sub.2C.sub.2 H.sub.5                          (CH.sub.2).sub.6    C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       (CH.sub.2).sub.6    C(CH.sub.3).sub.2CH.sub.2Cl                               (CH.sub.2).sub.6    C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        (CH.sub.2).sub.6    CH.sub.2C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.6                                                                                   ##STR127##                                               (CH.sub.2).sub.6    CH.sub.2SCH.sub.3                                         (CH.sub.2).sub.6    CHC(CH.sub.3).sub.2                                       (CH.sub.2).sub.6                                                                                   ##STR128##                                               (CH.sub.2).sub.6                                                                                   ##STR129##                                               (CH.sub.2).sub.6                                                                                   ##STR130##                                               (CH.sub.2).sub.6                                                                                   ##STR131##                                               (CH.sub.2).sub.6                                                                                   ##STR132##                                               (CH.sub.2).sub.6                                                                                   ##STR133##                                               (CH.sub.2).sub.7    CH.sub.3                                                  (CH.sub.2).sub.7    C.sub.2 H.sub.5                                           (CH.sub.2).sub.7    C.sub.3 H.sub.7 -n                                        (CH.sub.2).sub.7    C.sub.3 H.sub.7 -i                                        (CH.sub.2).sub.7    C.sub.4 H.sub.9 -n                                        (CH.sub.2).sub.7    C.sub.4 H.sub.9 -i                                        (CH.sub.2).sub.7    C.sub.4 H.sub.9 -t                                        (CH.sub.2).sub.7    C(CH.sub.3).sub.2C.sub.2 H.sub.5                          (CH.sub.2).sub.7    C(CH.sub.3).sub.2C.sub.3 H.sub.7 -i                       (CH.sub.2).sub.7    C(CH.sub.3).sub.2CH.sub.2Cl                               (CH.sub.2).sub.7    C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                        (CH.sub.2).sub.7    CH.sub.2C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.7                                                                                   ##STR134##                                               (CH.sub.2).sub.7    CH.sub.2SCH.sub.3                                         (CH.sub.2).sub.7    CHC(CH.sub.3).sub.2                                       (CH.sub.2).sub.7                                                                                   ##STR135##                                               (CH.sub.2).sub.7                                                                                   ##STR136##                                               (CH.sub.2).sub.7                                                                                   ##STR137##                                               (CH.sub.2).sub.7                                                                                   ##STR138##                                               (CH.sub.2).sub.7                                                                                   ##STR139##                                               (CH.sub.2).sub.7                                                                                   ##STR140##                                               ______________________________________                                    

The following compounds of the formula (Ic) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples:

                  TABLE 3                                                         ______________________________________                                         ##STR141##                    I-c                                            A        B       L        M   R.sup.2                                         ______________________________________                                        CH.sub.3 C.sub.2 H.sub.5                                                                       O        O   CH.sub.3                                        CH.sub.3 C.sub.2 H.sub.5                                                                       O        O   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.2 H.sub.5                                                                       O        O   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.2 H.sub.5                                                                       O        O   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.2 H.sub.5                                                                       O        O   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.2 H.sub.5                                                                       O        O   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.2 H.sub.5                                                                       O        O   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.2 H.sub.5                                                                       O        O   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.2 H.sub.5                                                                       O        O                                                                                  ##STR142##                                     CH.sub.3 C.sub.2 H.sub.5                                                                       O        O                                                                                  ##STR143##                                     CH.sub.3 C.sub.2 H.sub.5                                                                       O        O                                                                                  ##STR144##                                     CH.sub.3 C.sub.2 H.sub.5                                                                       O        S   CH.sub.3                                        CH.sub.3 C.sub.2 H.sub.5                                                                       O        S   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.2 H.sub.5                                                                       O        S   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.2 H.sub.5                                                                       O        S   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.2 H.sub.5                                                                       O        S   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.2 H.sub.5                                                                       O        S   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.2 H.sub.5                                                                       O        S   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.2 H.sub.5                                                                       O        S   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.3 H.sub.7                                                                       O        O   CH.sub.3                                        CH.sub.3 C.sub.3 H.sub.7                                                                       O        O   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.3 H.sub.7                                                                       O        O   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.3 H.sub.7                                                                       O        O   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.3 H.sub.7                                                                       O        O   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.3 H.sub.7                                                                       O        O   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.3 H.sub.7                                                                       O        O   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.3 H.sub.7                                                                       O        O   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.3 H.sub.7                                                                       O        O                                                                                  ##STR145##                                     CH.sub.3 C.sub.3 H.sub.7                                                                       O        O                                                                                  ##STR146##                                     CH.sub.3 C.sub.3 H.sub.7                                                                       O        O                                                                                  ##STR147##                                     CH.sub.3 C.sub.3 H.sub.7                                                                       O        S   CH.sub.3                                        CH.sub.3 C.sub.3 H.sub.7                                                                       O        S   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.3 H.sub.7                                                                       O        S   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.3 H.sub.7                                                                       O        S   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.3 H.sub.7                                                                       O        S   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.3 H.sub.7                                                                       O        S   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.3 H.sub.7                                                                       O        S   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.3 H.sub.7                                                                       O        S   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O   CH.sub.3                                        CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O                                                                                  ##STR148##                                     CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O                                                                                  ##STR149##                                     CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        O                                                                                  ##STR150##                                     CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        S   CH.sub.3                                        CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        S   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        S   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        S   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        S   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        S   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        S   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.3 H.sub.7 -i                                                                    O        S   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.4 H.sub.9                                                                       O        O   CH.sub.3                                        CH.sub.3 C.sub.4 H.sub.9                                                                       O        O   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.4 H.sub.9                                                                       O        O   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.4 H.sub.9                                                                       O        O   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.4 H.sub.9                                                                       O        O   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.4 H.sub.9                                                                       O        O   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.4 H.sub.9                                                                       O        O   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.4 H.sub.9                                                                       O        O   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.4 H.sub.9                                                                       O        O                                                                                  ##STR151##                                     CH.sub.3 C.sub.4 H.sub.9                                                                       O        O                                                                                  ##STR152##                                     CH.sub.3 C.sub.4 H.sub.9                                                                       O        O                                                                                  ##STR153##                                     CH.sub.3 C.sub.4 H.sub.9                                                                       O        S   CH.sub.3                                        CH.sub.3 C.sub.4 H.sub.9                                                                       O        S   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.4 H.sub.9                                                                       O        S   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.4 H.sub.9                                                                       O        S   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.4 H.sub.9                                                                       O        S   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.4 H.sub.9                                                                       O        S   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.4 H.sub.9                                                                       O        S   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.4 H.sub.9                                                                       O        S   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O   CH.sub.3                                        CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O                                                                                  ##STR154##                                     CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O                                                                                  ##STR155##                                     CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        O                                                                                  ##STR156##                                     CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        S   CH.sub.3                                        CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        S   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        S   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        S   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        S   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        S   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        S   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.4 H.sub.9 -i                                                                    O        S   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O   CH.sub.3                                        CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O                                                                                  ##STR157##                                     CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O                                                                                  ##STR158##                                     CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        O                                                                                  ##STR159##                                     CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        S   CH.sub.3                                        CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        S   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        S   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        S   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        S   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        S   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        S   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.4 H.sub.9 -s                                                                    O        S   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O   CH.sub.3                                        CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O   CH.sub.2C.sub.4 H.sub.9 -t                      CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O                                                                                  ##STR160##                                     CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O                                                                                  ##STR161##                                     CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        O                                                                                  ##STR162##                                     CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        S   CH.sub.3                                        CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        S   C.sub.2 H.sub.5                                 CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        S   C.sub.3 H.sub.7                                 CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        S   C.sub.3 H.sub.7 -i                              CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        S   C.sub.4 H.sub.9 -i                              CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        S   C.sub.4 H.sub.9 -s                              CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        S   C.sub.4 H.sub.9 -t                              CH.sub.3 C.sub.4 H.sub.9 -t                                                                    O        S   CH.sub.2C.sub.4 H.sub.9 -t                      C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O   CH.sub.3                                        C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O   C.sub.2 H.sub.5                                 C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O   C.sub.3 H.sub.7                                 C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O   C.sub.3 H.sub.7 -i                              C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O   C.sub.4 H.sub.9 -i                              C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O   C.sub.4 H.sub.9 -s                              C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O   C.sub.4 H.sub.9 -t                              C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O   CH.sub.2C.sub.4 H.sub.9 -t                      C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O                                                                                  ##STR163##                                     C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O                                                                                  ##STR164##                                     C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        O                                                                                  ##STR165##                                     C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        S   CH.sub.3                                        C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        S   C.sub.2 H.sub.5                                 C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        S   C.sub.3 H.sub.7                                 C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        S   C.sub.3 H.sub.7 -i                              C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        S   C.sub.4 H.sub.9 -i                              C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        S   C.sub.4 H.sub.9 -s                              C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        S   C.sub.4 H.sub.9 -t                              C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                       O        S   CH.sub.2C.sub.4 H.sub.9 -t                      (CH.sub.2).sub.2                                                                           O        O     CH.sub.3                                          (CH.sub.2).sub.2                                                                           O        O     C.sub.2 H.sub.5                                   (CH.sub.2).sub.2                                                                           O        O     C.sub.3 H.sub.7                                   (CH.sub.2).sub.2                                                                           O        O     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.2                                                                           O        O     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.2                                                                           O        O     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.2                                                                           O        O     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.2                                                                           O        O     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.2                                                                           O        O                                                                                    ##STR166##                                       (CH.sub.2).sub.2                                                                           O        O                                                                                    ##STR167##                                       (CH.sub.2).sub.2                                                                           O        O                                                                                    ##STR168##                                       (CH.sub.2).sub.2                                                                           O        S     CH.sub.3                                          (CH.sub.2).sub.2                                                                           O        S     C.sub.2 H.sub.5                                   (CH.sub.2).sub.2                                                                           O        S     C.sub.3 H.sub.7                                   (CH.sub.2).sub.2                                                                           O        S     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.2                                                                           O        S     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.2                                                                           O        S     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.2                                                                           O        S     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.2                                                                           O        S     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.4                                                                           O        O     CH.sub.3                                          (CH.sub.2).sub.4                                                                           O        O     C.sub.2 H.sub.5                                   (CH.sub.2).sub.4                                                                           O        O     C.sub.3 H.sub.7                                   (CH.sub.2).sub.4                                                                           O        O     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.4                                                                           O        O     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.4                                                                           O        O     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.4                                                                           O        O     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.4                                                                           O        O     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.4                                                                           O        O                                                                                    ##STR169##                                       (CH.sub.2).sub.4                                                                           O        O                                                                                    ##STR170##                                       (CH.sub.2).sub.4                                                                           O        O                                                                                    ##STR171##                                       (CH.sub.2).sub.4                                                                           O        S     CH.sub.3                                          (CH.sub.2).sub.4                                                                           O        S     C.sub.2 H.sub.5                                   (CH.sub.2).sub.4                                                                           O        S     C.sub.3 H.sub.7                                   (CH.sub.2).sub.4                                                                           O        S     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.4                                                                           O        S     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.4                                                                           O        S     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.4                                                                           O        S     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.4                                                                           O        S     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.5                                                                           O        O     CH.sub.3                                          (CH.sub.2).sub.5                                                                           O        O     C.sub.2 H.sub.5                                   (CH.sub.2).sub.5                                                                           O        O     C.sub.3 H.sub.7                                   (CH.sub.2).sub.5                                                                           O        O     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.5                                                                           O        O     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.5                                                                           O        O     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.5                                                                           O        O     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.5                                                                           O        O     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.5                                                                           O        O                                                                                    ##STR172##                                       (CH.sub.2).sub.5                                                                           O        O                                                                                    ##STR173##                                       (CH.sub.2).sub.5                                                                           O        O                                                                                    ##STR174##                                       (CH.sub.2).sub.5                                                                           O        S     CH.sub.3                                          (CH.sub.2).sub.5                                                                           O        S     C.sub.2 H.sub.5                                   (CH.sub.2).sub.5                                                                           O        S     C.sub.3 H.sub.7                                   (CH.sub.2).sub.5                                                                           O        S     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.5                                                                           O        S     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.5                                                                           O        S     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.5                                                                           O        S     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.5                                                                           O        S     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.6                                                                           O        O     CH.sub.3                                          (CH.sub.2).sub.6                                                                           O        O     C.sub.2 H.sub.5                                   (CH.sub.2).sub.6                                                                           O        O     C.sub.3 H.sub.7                                   (CH.sub.2).sub.6                                                                           O        O     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.6                                                                           O        O     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.6                                                                           O        O     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.6                                                                           O        O     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.6                                                                           O        O     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.6                                                                           O        O                                                                                    ##STR175##                                       (CH.sub.2).sub.6                                                                           O        O                                                                                    ##STR176##                                       (CH.sub.2).sub.6                                                                           O        O                                                                                    ##STR177##                                       (CH.sub.2).sub.6                                                                           O        S     CH.sub.3                                          (CH.sub.2).sub.6                                                                           O        S     C.sub.2 H.sub.5                                   (CH.sub.2).sub.6                                                                           O        S     C.sub.3 H.sub.7                                   (CH.sub.2).sub.6                                                                           O        S     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.6                                                                           O        S     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.6                                                                           O        S     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.6                                                                           O        S     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.6                                                                           O        S     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.7                                                                           O        O     CH.sub.3                                          (CH.sub.2).sub.7                                                                           O        O     C.sub.2 H.sub.5                                   (CH.sub.2).sub.7                                                                           O        O     C.sub.3 H.sub.7                                   (CH.sub.2).sub.7                                                                           O        O     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.7                                                                           O        O     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.7                                                                           O        O     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.7                                                                           O        O     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.7                                                                           O        O     CH.sub.2C.sub.4 H.sub.9 -t                        (CH.sub.2).sub.7                                                                           O        O                                                                                    ##STR178##                                       (CH.sub.2).sub.7                                                                           O        O                                                                                    ##STR179##                                       (CH.sub.2).sub.7                                                                           O        O                                                                                    ##STR180##                                       (CH.sub.2).sub.7                                                                           O        S     CH.sub.3                                          (CH.sub.2).sub.7                                                                           O        S     C.sub.2 H.sub.5                                   (CH.sub.2).sub.7                                                                           O        S     C.sub.3 H.sub.7                                   (CH.sub.2).sub.7                                                                           O        S     C.sub.3 H.sub.7 -i                                (CH.sub.2).sub.7                                                                           O        S     C.sub.4 H.sub.9 -i                                (CH.sub.2).sub.7                                                                           O        S     C.sub.4 H.sub.9 -s                                (CH.sub.2).sub.7                                                                           O        S     C.sub.4 H.sub.9 -t                                (CH.sub.2).sub.7                                                                           O        S     CH.sub.2C.sub.4 H.sub.9 -t                        ______________________________________                                    

The following compounds of the formula (Id) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples:

                  TABLE 4                                                         ______________________________________                                         ##STR181##                    I-d                                            A               B       R.sup.3                                               ______________________________________                                        CH.sub.3        C.sub.2 H.sub.5                                                                       CH.sub.3                                              CH.sub.3        C.sub.3 H.sub.7 -n                                                                    CH.sub.3                                              CH.sub.3        C.sub.3 H.sub.7 -i                                                                    CH.sub.3                                              CH.sub.3        C.sub.4 H.sub.9-n                                                                     CH.sub.3                                              CH.sub.3        C.sub.4 H.sub.9 -i                                                                    CH.sub.3                                              CH.sub.3        C.sub.4 H.sub.9 -s                                                                    CH.sub.3                                              CH.sub.3        C.sub.4 H.sub.9 -t                                                                    CH.sub.3                                              CH.sub.3        C.sub.5 H.sub.11                                                                      CH.sub.3                                              CH.sub.3        C.sub.5 H.sub.11 -i                                                                   CH.sub.3                                              C.sub.2 H.sub.5 C.sub.2 H.sub.5                                                                       CH.sub.3                                              C.sub.3 H.sub.7 -n                                                                            C.sub.3 H.sub.7                                                                       CH.sub.3                                              C.sub.3 H.sub.7 -i                                                                            C.sub.3 H.sub.7 -i                                                                    CH.sub.3                                              (CH.sub.2).sub.2    CH.sub.3                                                  (CH.sub.2).sub.4    CH.sub.3                                                  (CH.sub.2).sub.5    CH.sub.3                                                  (CH.sub.2).sub.6    CH.sub.3                                                  (CH.sub.2).sub.7    CH.sub.3                                                  ______________________________________                                    

The following compounds of the formula (Ie) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples:

                  TABLE 5                                                         ______________________________________                                         ##STR182##                    I-e                                            A    B       L      R.sup.4   R.sup.5                                         ______________________________________                                        CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  OCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3                                                                                 ##STR183##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3                                                                                 ##STR184##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3                                                                                 ##STR185##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  SCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      CH.sub.3  SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         OCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                          ##STR186##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                          ##STR187##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                          ##STR188##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         SCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      C.sub.2 H.sub.5                                                                         SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  OCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3                                                                                 ##STR189##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3                                                                                 ##STR190##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3                                                                                 ##STR191##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  SCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      CH.sub.3  SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         OCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                          ##STR192##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                          ##STR193##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                          ##STR194##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         SCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      C.sub.2 H.sub.5                                                                         SCH.sub.2C.sub.4 H.sub.9 -t                     (CH.sub.2).sub.5                                                                       O      CH.sub.3    OCH.sub.3                                         (CH.sub.2).sub.5                                                                       O      CH.sub.3    OC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       O      CH.sub.3    OC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       O      CH.sub.3    OC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       O      CH.sub.3    OC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       O      CH.sub.3    OC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       O      CH.sub.3    OC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       O      CH.sub.3    OCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       O      CH.sub.3                                                                                   ##STR195##                                       (CH.sub.2).sub.5                                                                       O      CH.sub.3                                                                                   ##STR196##                                       (CH.sub.2).sub.5                                                                       O      CH.sub.3                                                                                   ##STR197##                                       (CH.sub.2).sub.5                                                                       O      CH.sub.3    SCH.sub.3                                         (CH.sub.2).sub.5                                                                       O      CH.sub.3    SC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       O      CH.sub.3    SC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       O      CH.sub.3    SC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       O      CH.sub.3    SC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       O      CH.sub.3    SC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       O      CH.sub.3    SC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       O      CH.sub.3    SCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           OCH.sub.3                                         (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           OC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           OC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           OC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           OC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           OC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           OC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           OCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                            ##STR198##                                       (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                            ##STR199##                                       (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                            ##STR200##                                       (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SCH.sub.3                                         (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SCH.sub.2C.sub.4 H.sub.9 -t                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 OCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3                                                                                ##STR201##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3                                                                                ##STR202##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3                                                                                ##STR203##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 SCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OCH.sub.3 SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                         ##STR204##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                         ##STR205##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                         ##STR206##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        SCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       O      OC.sub.2 H.sub.5                                                                        SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 OCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3                                                                                ##STR207##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3                                                                                ##STR208##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3                                                                                ##STR209##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 SCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OCH.sub.3 SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                         ##STR210##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                         ##STR211##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                         ##STR212##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        SCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    O      OC.sub.2 H.sub.5                                                                        SCH.sub.2C.sub.4 H.sub.9 -t                     (CH.sub.2).sub.5                                                                       O      OCH.sub.3   OCH.sub.3                                         (CH.sub.2).sub.5                                                                       O      OCH.sub.3   OC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       O      OCH.sub.3   OC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       O      OCH.sub.3   OC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       O      OCH.sub.3   OC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       O      OCH.sub.3   OC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       O      OCH.sub.3   OC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       O      OCH.sub.3   OCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       O      OCH.sub.3                                                                                  ##STR213##                                       (CH.sub.2).sub.5                                                                       O      OCH.sub.3                                                                                  ##STR214##                                       (CH.sub.2).sub.5                                                                       O      OCH.sub.3                                                                                  ##STR215##                                       (CH.sub.2).sub.5                                                                       O      OCH.sub.3   SCH.sub.3                                         (CH.sub.2).sub.5                                                                       O      OCH.sub.3   SC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       O      OCH.sub.3   SC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       O      OCH.sub.3   SC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       O      OCH.sub.3   SC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       O      OCH.sub.3   SC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       O      OCH.sub.3   SC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       O      OCH.sub.3   SCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          OCH.sub.3                                         (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          OC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          OC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          OC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          OC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          OC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          OCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                           ##STR216##                                       (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                           ##STR217##                                       (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                           ##STR218##                                       (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          SCH.sub.3                                         (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          SC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          SC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          SC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          SC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       O      OC.sub.2 H.sub.5                                                                          SC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       O      C.sub.2 H.sub.5                                                                           SCH.sub.2C.sub.4 H.sub.9 -t                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  OCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3                                                                                 ##STR219##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3                                                                                 ##STR220##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3                                                                                 ##STR221##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  SCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      CH.sub.3  SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         OCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                          ##STR222##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                          ##STR223##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                          ##STR224##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         SCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      C.sub.2 H.sub.5                                                                         SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  OCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3                                                                                 ##STR225##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3                                                                                 ##STR226##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3                                                                                 ##STR227##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  SCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      CH.sub.3  SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         OCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                          ##STR228##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                          ##STR229##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                          ##STR230##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         SCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      C.sub.2 H.sub.5                                                                         SCH.sub.2C.sub.4 H.sub.9 -t                     (CH.sub.2).sub.5                                                                       S      CH.sub.3    OCH.sub.3                                         (CH.sub.2).sub.5                                                                       S      CH.sub.3    OC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       S      CH.sub.3    OC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       S      CH.sub.3    OC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       S      CH.sub.3    OC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       S      CH.sub.3    OC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       S      CH.sub.3    OC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       S      CH.sub.3    OCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       S      CH.sub.3                                                                                   ##STR231##                                       (CH.sub.2).sub.5                                                                       S      CH.sub.3                                                                                   ##STR232##                                       (CH.sub.2).sub.5                                                                       S      CH.sub.3                                                                                   ##STR233##                                       (CH.sub.2).sub.5                                                                       S      CH.sub.3    SCH.sub.3                                         (CH.sub.2).sub.5                                                                       S      CH.sub.3    SC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       S      CH.sub.3    SC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       S      CH.sub.3    SC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       S      CH.sub.3    SC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       S      CH.sub.3    SC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       S      CH.sub.3    SC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       S      CH.sub.3    SCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           OCH.sub.3                                         (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           OC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           OC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           OC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           OC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           OC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           OC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           OCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                            ##STR234##                                       (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                            ##STR235##                                       (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                            ##STR236##                                       (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           SCH.sub.3                                         (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           SC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           SC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           SC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           SC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           SC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           SC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       S      C.sub.2 H.sub.5                                                                           SCH.sub.2C.sub.4 H.sub.9 -t                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 OCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3                                                                                ##STR237##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3                                                                                ##STR238##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3                                                                                ##STR239##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 SCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OCH.sub.3 SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                         ##STR240##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                         ##STR241##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                         ##STR242##                                     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        SCH.sub.3                                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.2 H.sub.5                                                                       S      OC.sub.2 H.sub.5                                                                        SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 OCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3                                                                                ##STR243##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3                                                                                ##STR244##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3                                                                                ##STR245##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 SCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OCH.sub.3 SCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        OC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        OC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        OC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        OCH.sub.2C.sub.4 H.sub.9 -t                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                         ##STR246##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                         ##STR247##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                         ##STR248##                                     CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        SCH.sub.3                                       CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        SC.sub.2 H.sub.5                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        SC.sub.3 H.sub.7                                CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        SC.sub.3 H.sub.7 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -i                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -s                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        SC.sub.4 H.sub.9 -t                             CH.sub.3                                                                           C.sub.3 H.sub.7 -i                                                                    S      OC.sub.2 H.sub.5                                                                        SCH.sub.2C.sub.4 H.sub.9 -t                     (CH.sub.2).sub.5                                                                       S      OCH.sub.3   OCH.sub.3                                         (CH.sub.2).sub.5                                                                       S      OCH.sub.3   OC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       S      OCH.sub.3   OC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       S      OCH.sub.3   OC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       S      OCH.sub.3   OC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       S      OCH.sub.3   OC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       S      OCH.sub.3   OC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       S      OCH.sub.3   OCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       S      OCH.sub.3                                                                                  ##STR249##                                       (CH.sub.2).sub.5                                                                       S      OCH.sub.3                                                                                  ##STR250##                                       (CH.sub.2).sub.5                                                                       S      OCH.sub.3                                                                                  ##STR251##                                       (CH.sub.2).sub.5                                                                       S      OCH.sub.3   SCH.sub.3                                         (CH.sub.2).sub.5                                                                       S      OCH.sub.3   SC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       S      OCH.sub.3   SC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       S      OCH.sub.3   SC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       S      OCH.sub.3   SC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       S      OCH.sub.3   SC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       S      OCH.sub.3   SC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       S      OCH.sub.3   SCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          OCH.sub.3                                         (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          OC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          OC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          OC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          OC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          OC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          OCH.sub.2C.sub.4 H.sub.9 -t                       (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                           ##STR252##                                       (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                           ##STR253##                                       (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                           ##STR254##                                       (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          SCH.sub.3                                         (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          SC.sub.2 H.sub.5                                  (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          SC.sub.3 H.sub.7                                  (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          SC.sub.3 H.sub.7 -i                               (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          SC.sub.4 H.sub.9 -i                               (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          SC.sub.4 H.sub.9 -s                               (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          SC.sub.4 H.sub.9 -t                               (CH.sub.2).sub.5                                                                       S      OC.sub.2 H.sub.5                                                                          SCH.sub.2C.sub.4 H.sub.9 -t                       ______________________________________                                    

The following compounds of the formula (If) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples:

                  TABLE 6                                                         ______________________________________                                         ##STR255##                    I-f                                            A              B       E.sup.•                                          ______________________________________                                        CH.sub.3       C.sub.2 H.sub.5                                                                       i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.3 H.sub.7 -n                                                                    i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.3 H.sub.7 -i                                                                    i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.4 H.sub.9-n                                                                     i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.4 H.sub.9 -i                                                                    i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.4 H.sub.9 -s                                                                    i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.4 H.sub.9 -t                                                                    i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.5 H.sub.11                                                                      i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.5 H.sub.11-i                                                                    i-C.sub.3 H.sub.7 NH.sub.3                             C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                                                       i-C.sub.3 H.sub.7 NH.sub.3                             CH.sub.3       C.sub.3 H.sub.7                                                                       i-C.sub.3 H.sub.7 NH.sub.3                             C.sub.3 H.sub.7 -i                                                                           C.sub.3 H.sub.7 -i                                                                    i-C.sub.3 H.sub.7 NH.sub.3                             (CH.sub.2).sub.2   i-C.sub.3 H.sub.7 NH.sub.3                                 (CH.sub.2).sub.4   i-C.sub.3 H.sub.7 NH.sub.3                                 (CH.sub.2).sub.5   i-C.sub.3 H.sub.7 NH.sub.3                                 (CH.sub.2).sub.6   i-C.sub.3 H.sub.7 NH.sub.3                                 (CH.sub.2).sub.7   i-C.sub.3 H.sub.7 NH.sub.3                                 CH.sub.3       C.sub.2 H.sub.5                                                                       Na                                                     CH.sub.3       C.sub.3 H.sub.7 -n                                                                    Na                                                     CH.sub.3       C.sub.3 H.sub.7 -i                                                                    Na                                                     CH.sub.3       C.sub.4 H.sub.9-n                                                                     Na                                                     CH.sub.3       C.sub.4 H.sub.9 -i                                                                    Na                                                     CH.sub.3       C.sub.4 H.sub.9 -s                                                                    Na                                                     CH.sub.3       C.sub.4 H.sub.9 -t                                                                    Na                                                     CH.sub.3       C.sub.5 H.sub.11                                                                      Na                                                     CH.sub.3       C.sub.5 H.sub.11-i                                                                    Na                                                     C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                                                       Na                                                     CH.sub.3       C.sub.3 H.sub.7                                                                       Na                                                     C.sub.3 H.sub.7 -i                                                                           C.sub.3 H.sub.7 -i                                                                    Na                                                     (CH.sub.2).sub.2   Na                                                         (CH.sub.2).sub.4   Na                                                         (CH.sub.2).sub.5   Na                                                         (CH.sub.2).sub.6   Na                                                         (CH.sub.2).sub.7   Na                                                         ______________________________________                                    

The following compounds o f the formula (Ig) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples:

                  TABLE 7                                                         ______________________________________                                         ##STR256##                    I-g                                            A       B           R.sup.6    R.sup.7                                        ______________________________________                                        CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.3 H.sub.7 -n                                                                        CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.3 H.sub.7 -i                                                                        CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.4 H.sub.9-n                                                                         CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.4 H.sub.9 -i                                                                        CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.4 H.sub.9 -s                                                                        CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.4 H.sub.9 -t                                                                        CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.5 H.sub.11                                                                          CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.5 H.sub.11-i                                                                        CH.sub.3   CH.sub.3                                       C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                           CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.3 H.sub.7                                                                           CH.sub.3   CH.sub.3                                       C.sub.3 H.sub.7 -i                                                                    C.sub.3 H.sub.7 -i                                                                        CH.sub.3   CH.sub.3                                       (CH.sub.2).sub.2    CH.sub.3   CH.sub.3                                       (CH.sub.2).sub.4    CH.sub.3   CH.sub.3                                       (CH.sub.2).sub.5    CH.sub.3   CH.sub.3                                       (CH.sub.2).sub.6    CH.sub.3   CH.sub.3                                       (CH.sub.2).sub.7    CH.sub.3   CH.sub.3                                       CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.3 H.sub.7 -n                                                                        (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.3 H.sub.7 -i                                                                        (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.4 H.sub.9-n                                                                         (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.4 H.sub.9 -i                                                                        (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.4 H.sub.9 -s                                                                        (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.4 H.sub.9 -t                                                                        (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.5 H.sub.11                                                                          (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.5 H.sub.11-i                                                                        (CH.sub.2).sub.2O(CH.sub.2).sub.2                         C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                           (CH.sub.2).sub.2O(CH.sub.2).sub.2                         CH.sub.3                                                                              C.sub.3 H.sub.7                                                                           (CH.sub.2).sub.2O(CH.sub.2).sub.2                         C.sub.3 H.sub.7 -i                                                                    C.sub.3 H.sub.7 -i                                                                        (CH.sub.2).sub.2O(CH.sub.2).sub.2                         (CH.sub.2).sub.2    (CH.sub.2).sub.2O(CH.sub.2).sub.2                         (CH.sub.2).sub.4    (CH.sub.2).sub.2O(CH.sub.2).sub.2                         (CH.sub.2).sub.5    (CH.sub.2).sub.2O(CH.sub.2).sub.2                         (CH.sub.2).sub.6    (CH.sub.2).sub.2O(CH.sub.2).sub.2                         (CH.sub.2).sub.7    (CH.sub.2).sub.2O(CH.sub.2).sub.2                         ______________________________________                                    

In addition to the intermediates mentioned in the preparation examples,the following compounds of the formula (II) may be mentioned by way ofexample but not by way of limitation:

Methyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylbutyrate,

Methyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylvalerate;

Methyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylisovalerate,

Methyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylcaproate,

Methyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylisocaprate,

Methyl N-(2,4-dimethylphenylacetyl)-2-amino-2,3-dimethylvalerate,

Methyl N-(2,4-dimethylphenylacetyl)-2-amino-2-ethylbutyrate,

Methyl N-(2,4-dimethylphenylacetyl)-1-amino-cyclopentanoate

Methyl N-(2,4-dimethylphenylacetyl)-1-amino-cyclohexanoate

Methyl N-(2,4-dimethylphenylacetyl)-1-amino-cycloheptanoate,

Methyl N-(2,4-dimethylphenylacetyl)-1-amino-cyclooctanoate,

Ethyl N-(2,4-dimethylphenyl acetyl)-2-amino-2-methylbutyrate,

Ethyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylvalerate;

Ethyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylisovalerate,

Ethyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylcaproate,

Ethyl N-(2,4-dimethylphenylacetyl)-2-amino-2-methylisocaproate,

Ethyl N-(2,4-dimethylphenylacetyl)-2-amino-2,3-dimethylvalerate,

Ethyl N-(2,4-dimethylphenylacetyl)-2-amino-2-ethylbutyrate,

Ethyl N-(2,4-dimethylphenylacetyl)-1-amino-cyclopentanoate

Ethyl N-(2,4-dimethylphenylacetyl)-1-amino-cyclohexanoate

Ethyl N-(2,4-dimethylphenylacetyl)-1-amino-cycloheptanoate,

Ethyl N-(2,4-dimethylphenylacetyl)-1-amino-cyclooctanoate,

In addition to the intermediates mentioned in the preparation examples,the following compounds of the formula (XVI) may be mentioned by way ofexample but not by limitation:

N-(2,4-dimethylphenylacetyl)-2-amino-2-methyl-butyronitrile,

N-(2,4-dimethylphenylacetyl)-2-amino-2-methyl-valeronitrile,

N-(2,4-dimethylphenylacetyl)-2-amino-2-methyl-isovaleronitrile,

N-(2,4-dimethylphenylacetyl)-2-amino-2-methyl-capronitrile;

N-(2,4-dimethylphenylacetyl)-2-amino-2-methyl-isocapronitrile,

N-(2,4-dimethylphenylacetyl)-2-amino-2,3-dimethyl-valeronitrile,

N-(2,4-dimethylphenylacetyl)-2-amino-2-ethyl-butyronitrile,

N-(2,4-dimethylphenylacetyl)-1-amino-cyclopentanonitrile,

N-(2,4-dimethylphenylacetyl)-1-amino-cyclohexanonitrile,

N-(2,4-dimethylphenylacetyl)-1-amino-cycloheptanonitrile,

N-(2,4-dimethylphenylacetyl)-1-amino-cyclooctanonitrile,

The acid halides of the formula (III), carboxylic anhydrides of theformula (IV), chloroformic esters or chloroformic thioesters of theformula (V), chloromonothioformic esters or chlorodithioformic esters ofthe formula (VI), alkyl halides of the formula (VII), sulphonylchlorides of the formula (VIII), phosphorus compounds of the formula(IX) and metal hydroxides or a mines of the formula (X) and (XI) andisocyanates or carbamoyl chlorides of the formula (XIII), all of whichare furthermore required as starting substances for carrying outprocesses (B), (C), (D), (E), (F), (G) and (H) according to theinvention, are generally known compounds of organic or inorganicchemistry.

Process (A) is characterized in that compounds of the formula (II), inwhich A, B and R⁸ have the above-mentioned meaning, are subjected tointramolecular condensation reaction in the presence of bases.

Diluents which can be employed in process (A) according to the inventionare all inert organic solvents. The following can preferably be used:hydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, isopropanol,butanol, iso-butanol and tert-butanol.

Bases (deprotonating agents) which can be employed when carrying outprocess (A) according to the invention are all customary protonacceptors. The following can preferably be used: alkali metal oxides,alkali metal hydroxides, alkali metal carbonates, alkaline earth metaloxides, alkaline earth metal hydroxides and alkaline earth metalcarbonates, such as sodium hydroxide, potassium hydroxide, magnesiumoxide, calcium oxide, sodium carbonate, potassium carbonate and calciumcarbonate, all of which can also be employed in the presence of phasetransfer catalysts, such as, for example, triethylbenzylammoniumchloride, tetrabutylammonium bromide, Adogen 464 or TDA 1*.sup.). Inaddition, alkali metals such as sodium or potassium can be employed.Other substances which can be employed are alkali metal amides, alkalimetal hydrides, alkaline earth metal amides and alkaline earth metalhydrides, such as sodium amide, sodium hydride and calcium hydride,moreover alkali metal alcoholates, such as sodium methylate, sodiumethylate and potassium tert.-butylate.

When carrying out process (A) according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures between 0° C. and 250° C.,preferably between 50° C. and 150° C.

In general, process (A) according to the invention is carried out underatmospheric pressure.

When carrying out process (A) according to the invention, the reactantsof the formulae (II) and the deprotonating bases are generally employedin twice the equimolar amounts. However, it is also possible to use oneor the other reactant in a larger excess (up to 3 mol).

Process (Bα) is characterized in that compounds of the formula (Ia) arereacted with carboxylic acid halides of the formula (III).

If the acid halides are used in process (Bα) according to the invention,then diluents which can be employed are all solvents which are inerttowards these compounds. The following can preferably be used:hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin,furthermore halogenohydrocarbons, such as methylene chloride,chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene,moreover ketones, such as acetone and methyl isopropyl ketone,furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane,in addition carboxylic esters, such as ethyl acetate, and also stronglypolar solvents, such as dimethyl sulphoxide and sulpholane. If the acidhalide is sufficiently stable to hydrolysis, the reaction can also becarried out in the presence of water.

If the corresponding carboxylic acid halides are used, then acid-bindingagents which are suitable for the reaction in accordance with process(Bα) according to the invention are all customary acid acceptors. Thefollowing can preferably be used: tertiary amines, such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), H unig base andN,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, moreover alkali metal carbonates andalkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate, and also alkali metal hydroxides, suchas sodium hydroxide and potassium hydroxide.

When carrying out process (Bα) according to the invention, the reactiontemperatures can also be varied within a substantial range, which alsoapplies if carboxylic acid halides are used. In general, the process iscarried out at temperatures between -20° C. and +150° C., preferablybetween 0° C. and 100° C.

When carrying out process (Bα) according to the invention, the startingsubstances of the formula (Ia) and the carboxylic acid halide of theformula (III) are generally used in approximately equivalent amounts.However, it is also possible to employ the carboxylic acid halide in alarger excess (up to 5 mol). Working-up is carried out by customarymethods.

Process (Bβ) is characterized in that compounds of the formula (Ia) arereacted with carboxylic anhydrides of the formula (IV).

If, in process (Bβ) according to the invention, carboxylic anhydridesare used as reactants of the formula (IV), then diluents which canpreferably be used are those which are also preferably suitable whenacid halides are used. Besides, a carboxylic anhydride employed inexcess can also simultaneously act as the diluent.

When carrying out process (Bβ) according to the invention, the reactiontemperatures can be varied within a substantial range, which alsoapplies if carboxylic anhydrides are used. In general, the process iscarried out at temperatures between -20° C. and +150° C., preferablybetween 0° C. and 100° C.

When carrying out the process according to the invention, the startingsubstances of the formula (Ia) and the carboxylic anhydride of theformula (IV) are generally used in approximately equivalent amounts.However, it is also possible to employ the carboxylic anhydride in alarger excess (up to 5 mol). Working-up is carried out by customarymethods.

In general, a procedure is followed in which diluent and excesscarboxylic anhydride as well as the carboxylic acid which forms areremoved by distillation or by washing with an organic solvent or withwater.

Process (C) is characterized in that compounds of the formula (Ia) arereacted with chloroformic esters or chloroformic thioesters of theformula (V).

If the corresponding chloroformic esters or chloroformic thioesters areused, then acid-binding agents in the reaction in accordance withprocess (C) according to the invention are all customary acid acceptors.The following can preferably be used: tertiary amines, such astriethylamine, pyridine, DABCO, DBU, DBA, H unig base andN,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, furthermore alkali metal carbonatesand alkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate, and also alkali metal hydroxides, suchas sodium hydroxide and potassium hydroxide.

If the chloroformic esters or chloroformic thioesters are used, thendiluents which can be employed in process (C) according to the inventionare all solvents which are inert towards these compounds. The followingcan preferably be used: hydrocarbons, such as benzine, benzene, toluene,xylene and tetralin, furthermore halogenohydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, furthermore ketones, such as acetone and methylisopropyl ketone, moreover ethers, such as diethyl ether,tetrahydrofuran and dioxane, in addition carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholane.

If the chloroformic esters or chloroformic thioesters are used ascarboxylic acid derivatives of the formula (V), then the reactiontemperatures can be varied within a substantial range when carrying outprocess (C) according to the invention. If the process is carried out inthe presence of a diluent and of an acid-binding agent, then thereaction temperatures are generally between -20° C. and 100° C.,preferably between 0° C. and 50° C.

Process (C) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (C) according to the invention, the startingsubstances of the formula (Ia) and the chloroformic ester orchloroformic thioester of the formula (V) in question are generally usedin approximately equivalent amounts. However, it is also possible toemploy one or the other reactant in a larger excess (up to 2 mol).Working-up is then carried out by customary methods. In general, aprocedure is followed in which precipitated salts are removed and thereaction mixture which remains is concentrated by stripping off thediluent.

In preparation process (D), approximately 1 mol of chloromonothioformicester or chlorodithioformic ester of the formula (VI) is reacted at 0°to 120° C., preferably at 20° to 60° C., per mole of starting compoundof the formula (Ia).

Suitable diluents which may be added are all inert polar organicsolvents, such as ethers, amides sulphones or sulphoxides.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide and dimethylsulphide are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound Ia issynthesized by adding strong deprotonating agents, such as, for example,sodium hydride or potassium tertiary butylate, a further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases, sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine beingmentioned by way of example.

The reaction can be carried out under atmospheric pressure or underincreased pressure; it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

In preparation process (D.sub.β), the equimolar amount, or an excess, ofcarbon disulphide is added per mole of starting compound of the formula(Ia). This process is preferably carried out at temperatures from 0° to50° C. and, in particular, at 20° to 30° C.

Frequently, it is expedient to first prepare the corresponding salt fromthe compound of the formula (Ia) by adding a deprotonating agent (suchas, for example, potassium tertiary butylate or sodium hydride). Thecompound (Ia) is reacted with carbon disulphide until the formation ofthe intermediate is complete, for example after stirring for severalhours at room temperature.

The further reaction with the alkyl halide of the formula (VII) ispreferably carried out at 0° to 70° C., in particular at 20° to 50° C.At least the equimolar amount of alkyl halide is employed.

The process is carried out under atmospheric pressure or under increasedpressure, preferably under atmospheric pressure.

Again, working-up is carried out by customary methods.

In preparation process (E), approximately 1 mol of sulphonyl chloride(VIII) is reacted per mole of starting compound of the formula (Ia) at-20° to 150° C., preferably at 0° to 70° C.

Suitable diluents which may be added are all inert polar organicsolvents, such as ethers, amides, nitriles, sulphones, sulphoxides orhalogenated hydrocarbons, such as methylene chloride.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide, dimethylsulphide and methylen chloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound Ia issynthesized by adding strong deprotonating agents (such as, for example,sodium hydride or potassium tertiary butylate), a further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases, sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine beingmentioned by way of example.

The reaction can be carried out under atmospheric pressure or underincreased pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

To obtain compounds of the structure (Ie) 1 to 2, preferably 1 to 1.3mol of the phosphorus compound of the formula (IX) are rected inpreparation process (F) per mole of the compound (Ia) at temperaturesbetween -40° C. and 150° C., preferably between -10° and 110° C.

Suitable diluents which may be added are all inert, polar organicsolvents, such as ethers, amides, nitriles, alcohols, sulphides,sulphones, sulphoxides and the like.

Acetonitrile, dimethyl sulphoxide, tetrahydrofuran, dimethylformamide ormethylene chloride are preferably employed.

Suitable acid-binding agents which may be added are customary inorganicor organic bases, such as hydroxides or carbonates. Examples which my bementioned are sodium hydroxide, sodium carbonate, potassium carbonate,pyridine and triethylamine.

The reaction can be carried out under atmospheric pressure or underincreased pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods of organicChemistry. The end products obtained are preferably purified bycrystallization, chromatography or by so-called "incipientdistillation", i.e. removal of the volatile components in vacuo.

Process (G) is characterized in that compounds of the formula (Ia) arereacted with metal hydroxides (X) or amines (XI).

Diluents which can be employed in the process according to the inventionare, preferably, ethers, such as tetrahydrofuran, dioxane or diethylether, or else alcohols, such as methanol, ethanol, isopropanol, butalso water. Process (G) according to the invention is generally carriedout under atmospheric pressure. The reaction temperatures are generallybetween -20° C. and 100° C., preferably between 0° C. and 50° C.

In preparation process (H.sub.α), approximately 1 mol of isocyanate, orisothiocyanate, of the formula (XII) is reacted per mole of startingcompound of the formula (Ia) at 0° to 100° C., preferably at 20° to 50°C.

Suitable diluents which may be added are all inert organic solvents,such as ethers, amides, nitriles, sulphones or sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Catalysts which are very advantageously employed are organotincompounds, such as, for example, dibutyltin dilaurate. The process ispreferably carried out under atmospheric pressure.

In preparation process (H.sub.β), approximately 1 mol of carbamoylchloride of the formula (XIII) is reacted per mole of starting compoundof the formula (Ia) at 0° to 150° C., preferably at 20° to 70° C.

Suitable diluents which may be added are all inert polar organicsolvents, such as ethers, amides, sulphones or sulphoxides.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylenechloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound (Ia) issynthesized by adding strong deprotonating agents (such as, for example,sodium hydride or potassium tertiary butylate), the further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases, sodium hydroxide, sodiumcarbonate, potassium carbonate, triethylamine or pyridine beingmentioned by way of example.

The reaction can be carried out under atmospheric pressure or underincreased pressure, it is preferably carried out under atmosphericpressure. Working-up carried out by customary methods.

The active compounds are suitable for combating animal pests, preferablyarthropods and nematodes, in particular insects and arachnids, whichoccur in agriculture, in forests, in the protection of stored productsand of materials, and in the hygiene sector. They are active againstnormally sensitive and resistant species and against all or individualdevelopment stages. The above-mentioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus,Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilusspp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchusassimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenusspp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor,Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonsolstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The active compounds according to the invention are not only activeagainst plant, hygiene and stored product pests, but also, in theveterinary medicine sector, against animal parasites (ectoparasites andendoparasites), such as scaly ticks, Argasidae, scab mites, Trombidae,flies (stinging and sucking), parasitic fly larvae, lice, hair lice,bird lice, fleas and endoparasitic worms.

They are effective against normally sensitive and resistant types andstrains and against all parasitic and non-parasitic developmental stagesof the ectoparasites and endoparasites.

The active compounds according to the invention are distinguished by apowerful insecticidal and acaricidal activity.

They can be used particularly successfully for combating plant-damaginginsects, such as, for example, against the larvae of the green riceleafhopper (Nephotettix cincticips), against the larvae of the mustardbeetle (Phaedon cochleariae) or against the tobacco budworm (Heliothisvirescens).

Moreover, they can be used in an outstanding manner for combatingplant-damaging mites, such as, for example, against the greenhouse redspider mite (Tetranychus urticae) and against the fruit tree red spidermite (Panonychus ulmi).

The active compounds according to the invention can be also used asdefoliants, desiccants, agents for destroying broad-leaved plants and,especially, as weed-killers. By weeds, in the broadest sense, there areto be understood all plants which grow in locations where they areundesired. Whether the substances according to the invention act astotal or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Arena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves; nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective combating of weedsin annual cultures.

The active compounds according to the invention are highly suitable forselectively combating monocotyledon weeds in monocotyledon anddicotyledon cultures by the post-emergence method. For example, they canbe employed very successfully in soya beans or winter wheat forcontrolling grass weeds.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, or example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts andground natural mineral, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates, assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkyaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedye-stuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

For combating weeds, the active compounds according to the invention, assuch or in the form of their formulations, can also be used as mixtureswith known herbicides, finished formulations or tank mixes beingpossible.

Suitable herbicides for the mixtures are known herbicides, such as, forexample,1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4(1H,3H)-dione (AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea(METABENZTHIAZURON) for combating weeds in cereals;4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) forcombating weeds in sugar beet, and4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one(METRIBUZIN) for combating weeds in soya beans. Other suitableherbicides are 2,4-dichlorophenoxyacetic acid (2,4-D);4-(2,4-dichlorophenoxy) butyric acid (2,4-DB);2,4-dichlorophenoxypropionic acid (2,4-DP);3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl5-(2,4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX);3,5-dibromo-4-hydroxy-benzonitrile (BROMOXYNIL);2-chloro-N-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide(CHLORSULFURON); 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, itsmethyl or its ethyl ester (DICLOFOPMETHYL);4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN);2-{4-[(6-chloro-2-benzoxazolyl)-oxy]-phenoxy}-propanoic acid, its methylor its ethyl ester (FENOXAPROP);[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its1-methylheptyl ester (FLUROXYPYR); methyl2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4(5)-methylbenzoate(IMAZAMETHABENZ); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL);N,N-dimethyl-N'-(4-isopropylphenyl)urea (ISOPROTURON);(2-methyl-4-chlorophenoxy)acetic acid (MCPA);(4-chloro-2-methylphenoxy)-propionic acid (MCPP);N-methyl-2-(1,3-benzothiazol-2-yloxy)acetanilide (MEFENACET);2-{[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino)-carbonyl]-amino]-sulphonyl}-benzoicacid or its (METSULFURON);N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN);φ-(6-chloro-3-phenyl-pyridazin-4-yl)-S-octyl thiocarbonate (PYRIDATE);4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TERBUTRYNE); and3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate(THIAMETURON). Surprisingly, some mixtures also show synergistic action.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 0.01 and 10 kg of active compound perhectare of soil surface, preferably between 0.05 and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES

Example (Ia-1): ##STR257##

67.6 g (0.223 mol) of methylN-(2,4-dimethylphenylacetyl)-1-amino-cyclohexanecarboxylate, dissolvedin 450 ml of absolute toluene, are added dropwise to a suspension of13.38 g (0.446 mol) of sodium hydride in 220 ml of absolute toluene, atboiling heat. The batch is refluxed until starting material is no longerdetectable by thin-layer chromatography. Then, ethanol is added dropwisewith ice-bath cooling until the evolution of hydrogen has ceased. Thesolvent is evaporated in vacuo, the residue is taken up in ethanol, andthe mixture is acidified with 4N hydrochloric acid at 0° C. to 20° C.The precipitate which has separated out is filtered off with suction anddried. The resulting crude product is recrystallized fromchloroform/n-hexane (1:3).

60.4 g (100% of theory) of3-(2,4-dimethylphenyl)-5,5-pentamethylene-pyrrolidine-2,4-dione ofmelting point m.p. 223° C. are obtained.

Example (Ia-2): ##STR258##

Analogously to Example (Ia-1),3-(2,4-dimethylphenyl)-5-methyl-5-isopropyl-pyrrolidine-2,4-dione ofmelting point m.p. 115° C. is obtained.

Example (Ia-3):

Analogously to Example (Ia-1),3-(2,4-dimethylphenyl)-5-methyl-5-sec-butyl-pyrrolidine-2,4 dione ofmelting point 125° C. is obtained.

Example (Ib-1) ##STR259##

5.42 g (0.020 mol) of3-(2,4-dimethylphenyl)-5,5-pentamethyl-pyrrolidine-2,4-dione areintroduced into 70 ml of absolute dichloromethane, and the mixture istreated with 2.8 ml of triethylamine. 1.5 ml of acetyl chloride in 5 mlof absolute dichloromethane are added at 0°-10° C. and stirring of thebatch is continued at room temperature. The end of the reaction isdetermined by thin-layer chromatography. The mixture is subsequentlywashed twice using in each case 200 ml of 0.5N sodium hydroxidesolution, the organic phase is dried over magnesium sulphate and thesolvent is stripped off in vacuo.

2.24 g (36% of theory) of3-(2,4-dimethylphenyl)-5,5-pentamethylene-4-acetoxy-Δ3-pyrrolin-2-one ofmelting point m.p. 224° C. are obtained.

The end products of the formula (I-b) which are listed in Table 8 beloware obtained analogously to Example (Ib-1) and following the generalinformation given in the description of the processes according to theinvention.

                  TABLE 8                                                         ______________________________________                                         ##STR260##                   (I-b)                                                                            Physical constant                            Ex. No. A      B        R.sup.1  (°C.)                                 ______________________________________                                        Ib-2    CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                      CH.sub.3 m.p.: 176                                    Ib-3    CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                      i-C.sub.3 H.sub.7                                                                      m.p.: 154                                    Ib-4    CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                      t-C.sub.4 H.sub.9                                                                      m.p.: 151                                    Ib-5    (CH.sub.2).sub.5                                                                          i-C.sub.3 H.sub.7                                                                        m.p.: 191                                      Ib-6    (CH.sub.2).sub.5                                                                          t-C.sub.4 H.sub.9                                                                        m.p.: 193                                      Ib-7    CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                      C.sub.2 H.sub.5                                                                        m.p.: 118                                    Ib-8    CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                      C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                      m.p.: 152                                    Ib-9    CH.sub.3                                                                             s-C.sub.4 H.sub.9                                                                      CH.sub.3 m.p.: 90                                     Ib-10   CH.sub.3                                                                             s-C.sub.4 H.sub.9                                                                      i-C.sub.3 H.sub.7                                                                      oil                                          Ib-11   CH.sub.3                                                                             s-C.sub.4 H.sub.9                                                                      t-C.sub.4 H.sub.9                                                                      oil                                          ______________________________________                                    

Example (Ic-1) ##STR261##

5.42 g (0.020 mol) of3-(2,4-dimethylphenyl)-5,5-pentamethylene-pyrrolidine-2,4-dione areintroduced into 70 ml of absolute dichloromethane, and the mixture istreated with 2.8 ml of triethylamine. 2.73 g of sec.-butyl chloroformatein 5 ml of absolute dichloromethane are added at 0°-10° C. and stirringof the batch is continued at room temperature. The end of the reactionis determined by thin-layer chromatography. The mixture is subsequentlywashed twice using in each case 200 ml of 0.5N sodium hydroxidesolution, the organic phase is dried over magnesium sulphate and thesolvent is stripped off in vacuo.

1.97 g (26% of theory) of O-(sec.-butyl)O-[3-(2,4-dimethylphenyl)]-5,5-pentamethylene-Δ3-pyrrolin-4-yl-2-onecarbonate of melting point m.p. 169° C. are obtained.

The end products of the formula (Ic) listed in Table 9 below areobtained analogously to Example (Ic-1) and following the generalinformation given in the description of the processes according to theinvention

                  TABLE 9                                                         ______________________________________                                         ##STR262##                    I-c                                                                                  Physical constant                       Ex. No.                                                                              A      B       L    M   R.sup.2                                                                              (°C.)                            ______________________________________                                        Ic-2   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                     O    O   C.sub.2 H.sub.5                                                                      m.p.: 149                               Ic-3   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                     O    O   s-C.sub.4 H.sub.9                                                                    m.p.: 132                               Ic-4   (CH.sub.2).sub.5                                                                         O      O   C.sub.2 H.sub.5                                                                      m.p.: 181                                 Ic-5   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                     O    S   i-C.sub.3 H.sub.7                                                                    m.p.: 152-153                           Ic-6   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                     O    O   CH.sub.3                                                                             m.p.: 152                               Ic-7   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                     O    O   i-C.sub.3 H.sub.7                                                                    oil                                     Ic-8   CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                     O    O   i-C.sub.4 H.sub.9                                                                    m.p.: 36                                Ic-9   CH.sub.3                                                                             s-C.sub.4 H.sub.9                                                                     O    O   C.sub.2 H.sub.5                                                                      m.p.: 60                                Ic-10  CH.sub.3                                                                             s-C.sub.4 H.sub.9                                                                     O    O   s-C.sub.4H.sub.9                                                                     oil                                     ______________________________________                                    

Example (Ie-1) ##STR263##

2 g (7.7 mmol) of3-(2,4-dimethylphenyl)-5-isopropyl-5-methyl-pyrrolidine-2,4-dione areintroduced into 20 ml of absolute tetrahydrofurane, and the mixture istreated with 1.2 ml of triethylamine. 2.3 g ofethyl-isopentylmercapto-thiophosphonic acid chloride are added at roomtemperature then the mixture is stirred at 50° C. for 24 hours. Thereaction product is isolated by filtration over silica gel (eluenthexane/acetone 7/3) and evaporation of the solvent. 1.9 g (55.8% oftheory) of the compound of formula (Ie-1) are obtained. Melting point:98° C.

Example (Ie-2)

Analogously the compound of formula (Ie-2) of melting point 116° C. isobtained. ##STR264## Example (Ig-1) ##STR265##

3.89 g (0.015 mol) of3-(2,4-dimethylphenyl)-5-isopropyl-5-methyl-pyrrolidine-2,4-dione areintroduced into 70 ml of absolute dichloromethane, and the mixture istreated with 2.1 ml (0.015 mol) of triethylamine. 1.76 ml (0.015 mol) ofmorpholinecarbamoyl chloride in 5 ml of absolute dichloromethane and 20ml of 4-N,N-dimethylaminopyridine (Steglich base) are added at 0°-10° C.The reaction mixture is refluxed and the end of the reaction isdetermined by thin-layer chromatography. The mixture is washed twiceusing 100 ml of 0.5N sodium hydroxide solution, the organic phase isdried over magnesium sulphate and the solvent is stripped off in vacuo.

After recrystallization from methyl tert.-buthyl ether/n-hexane, 4.4 g(79% of theory) of4-morpholinecarbamoyl-[3-(2,4-dimethylphenyl)-5-isopropyl-5-methyl-Δ3-pyrrolin-2-oneof melting point m.p. 152°-153° C. are obtained.

Example (Ig-2) ##STR266##

Analogously to Example (Ig-1)4-dimethylcarbamoyl-[3-(2,4-dimethylphenyl)]-5-isopropyl-5-methyl-Δ3-pyrrolin-2-oneof melting point m.p. 220° C. is obtained. below were employed ascomparison substances: ##STR267##3-(2,4-Dichlorophenyl)-5-methyl-5-isopropyl-pyrrolidine-2,4-dione,disclosed in EP 456,063 ##STR268##3-(2,4-Dichlorophenyl)-5-methyl-5-isopropyl-4-acetoxy-Δ3-pyrrolin-2-one,disclosed in EP 456,063 ##STR269##O-(sec.-butyl)-O-[3-(2,4-dichlorophenyl)]-5-methyl-5-isopropyl-Δ3-pyrrolin-4-yl-2-onecarbonate, disclosed in EP 456,063 ##STR270##O-(ethyl)-O-[3-(2,4-dichlorophenyl)]-5-methyl-5-isopropyl-Δ3-pyrrolin-4-yl-2-onecarbonate, disclosed in EP 456,063 ##STR271##3-(2,4,6-Trimethylphenyl)-5-methyl-5-isopropyl-pyrrolidine-2,4-dione,disclosed in EP 456,063

Example A

Post-emergence test

    ______________________________________                                        Solvent:  5 parts by weight of acetone                                        Emulsifier:                                                                             1 part by weight of alkylaryl polyglycol ether                      ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen so that the particularamounts of active compound desired are applied in 2,000 1 of water/ha.After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, a clearly superior activity and crop plant selectivitycompared with the prior art is shown, for example, by the compounds ofPreparation Example (Ia-2), (Ib-2), (Ib-3), (Ic-2) and (Ic-3).

In this test the following results were obtained at an exemplaryapplication rate of 125 g/ha, the active compounds being tolerated wellto very well by soja beans:

    ______________________________________                                                          Compound of                                                 Plant   % Activity                                                                              Example No.      Preparation                                ______________________________________                                        Digitaria                                                                             >70       Ia-2, Ib-2, Ib-3, Ic-2, Ic-3                                Cynodon >40       Ia-2, Ib-2, Ib-3, Ic-2, Ic-3                                Setaria   90      Ia-2, Ib-2, Ib-3, Ic-2, Ic-3                                ______________________________________                                    

Example B

Phaedon larvae test

    ______________________________________                                        Solvent:  7 parts by weight of dimethylformamide                              Emulsifier:                                                                             1 part by weight of alkylaryl polyglycol ether                      ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae), while theleaves are still moist.

After the specified periods of time, the plants are infested withmustard beetle larvae (Phaedon cochleariae). After intervals of 7 days,the destruction in % is determined. 100% means that all the beetlelarvae have been killed; 0% means that none of the beetle larvae havebeen killed.

In this test, a destruction of 100% after 7 days is shown, for example,by the compounds of Preparation Examples (Ib-3) and (Ic-2) at anexemplary active compound concentration of 0.01%.

Example C

Heliothis virescens test

    ______________________________________                                        Solvent:  7 parts by weight of dimethylformamide                              Emulsifier:                                                                             1 part by weight of alkylaryl polyglycol ether                      ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated mount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soya bean shoots (Glycine max) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with tobacco budworm caterpillars (Heliothis virescens) whilethe leaves are still moist.

After the specified periods of time, the destruction in is determined.100% means that all animals have been killed; 0% means that none of thecaterpillars have been killed.

In this test, a destruction of 100% after 7 days is shown, for example,by the compounds of the Preparation Examples (Ib-5), (Ic-1), (Ic-3) and(Ic-4) at an exemplary active compound concentration of 0.1%.

Example D

Nephotettix test

    ______________________________________                                        Solvent:  7 parts by weight of dimethylformamide                              Emulsifier:                                                                             1 part by weight of alkylaryl polyglycol ether                      ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryzae sativa) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with larvae of the green rice leafhopper (Nephotettixcincticeps) while the leaves are still moist.

After the specified periods of time, the destruction in % is determined.100% means that all leafhoppers have been killed; 0% means that none ofthe leafhoppers have been killed.

In this test, a destruction of 100% after 7 days is shown, for example,by the compound of the Preparation Example (Ib-3) at an exemplary activecompound concentration of 0.01%.

Example E

Tetranychus test (OP resistant)

    ______________________________________                                        Solvent:  3 parts by weight of dimethylformamide                              Emulsifier:                                                                             1 part by weight of alkylaryl polyglycol ether                      ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested with alldevelopment stages of the greenhouse red spider mite or two-spottedspider mite (Tetranychus urticae) are treated by being dipped into thepreparation of active compound of the desired concentration.

After the specified periods of time, the destruction in % is determined.100% means that all spider mites have been killed; 0% means that none ofthe spider mites have been killed.

In this test, a destruction of 100% after 14 days is shown, for example,by the compounds of the Preparation Examples (Ib-5), (Ic-1), (Ic-2),(Ic-3) and (Ic-4) at an exemplary active compound concentration of0.02%.

Example F

Panonychus test

    ______________________________________                                        Solvent:  3 parts by weight of dimethylformamide                              Emulsifier:                                                                             1 part by weight of alkylaryl polyglycol ether                      ______________________________________                                    

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Young plant trees (Prunus domestica) which have an approximate height of30 cm and which are heavily infested with all development stages of thefruit tree red spider mite (Panonychus ulmi) are treated by being dippedinto the preparation of active compound of the desired concentration.

After the specified periods of time, the destruction in is determined.100% means that all spider mites have been killed; 0% means that none ofthe spider mites have been killed.

In this test, a destruction of 100% after 14 days is shown, for example,by the compounds of the Preparation Examples (Ib-3), (Ic-2) and (Ic-3)at an exemplary active compound concentration of 0.02%.

We claim:
 1. A dialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidine-2,4-dioneof the formula ##STR272## in which A represents alkyl which isoptionally substituted by halogen andB represents C₂ -C₁₀ -alkyl or Aand B together with the carbon atom to which they are bonded representan unsubstituted spiro carbocyclic ring, G represents hydrogen.
 2. Apesticidal or herbicidal composition which comprises an effective amountof a compound according to claim 1 and diluent.
 3. A method forcombatting pests or undesired plant overgrowth, which comprises applyingan effective amount of a compound according to claim 1, to a said pestor plant or to their environment.
 4. A compound according to claim 1,wherein such compound is ##STR273##
 5. A compound according to claim 1,wherein such compound is ##STR274##
 6. A compound according to claim 1,wherein such compound is ##STR275##
 7. The method according to claim 3,wherein such compound is ##STR276##